Polymer compound and light-emitting device using same

ABSTRACT

A polymer compound having a constitutional unit represented by the following formula (1):

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Section 371 of International Application No.PCT/JP2011/079592, filed Dec. 21, 2011, which was published in theJapanese language on Jun. 28, 2012, under International Publication No.WO 2012/086668 A1, and the disclosure of which is incorporated herein byreference.

TECHNICAL FIELD

The present invention relates to a polymer compound, its raw materialcompound, composition containing the polymer compound, a liquidcomposition containing the polymer compound, an organic film, alight-emitting device, and a display device.

BACKGROUND ART

As a light-emitting material used for the light-emitting device, apolymer compound including a constitutional unit derived from arylamine(Patent Literature 1) and a polymer compound including a constitutionalunit derived from fluorene (Patent Literature 2) have been examined, forexample.

CITATION LIST Patent Literature

-   Patent Literature 1: Japanese Patent Application Laid-Open No.    2004-143419-   Patent Literature 2: National Publication of International Patent    Application No. 2004-527628

SUMMARY OF INVENTION Technical Problem

However, in the light-emitting device using the conventional polymercompound, its luminance life is not always sufficient.

Then, the present invention is aimed to provide a polymer compounduseful for production of a light-emitting device whose luminance life isexcellent. The present invention is moreover aimed to provide acomposition containing the polymer compound, a liquid composition, anorganic film, a light-emitting element, a surface lighting source, and adisplay device. The present invention is further aimed to provide a rawmaterial compound for the polymer compound.

Solution to Problem

The present invention provides a polymer compound having aconstitutional unit represented by the following formula (1).

wherein n¹ and n² each independently represent an integer of 1 to 5; R¹,R², R³, R⁴, R⁵, R⁶, R⁸, R⁹ and R¹⁰ each independently represent ahydrogen atom, an unsubstituted or substituted alkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group,or an unsubstituted or substituted monovalent heterocyclic group; R^(A)and R^(B) each independently represent a hydrogen atom, an unsubstitutedor substituted alkyl group, an unsubstituted or substituted aryl group,or an unsubstituted or substituted monovalent heterocyclic group; Ar¹and Ar² each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or different groupsselected from arylene groups and divalent heterocyclic groups are linked(the group may have a substituent); when R¹, R², R³, and R⁴ exist inplural, the plurality of R¹, R², R³, or R⁴ may be the same or differentfrom each other; among R¹, R², R³, and R⁴, adjacent groups may be linkedto each other to form a ring structure; among R⁷, R⁸, R⁹ and R¹⁰,adjacent groups may be linked to each other to form a ring structure;Ar¹ and R^(A) may be linked to each other to form a ring structure; andAr² and R^(B) may be linked to each other to form a ring structure.

According to the polymer compound, a light-emitting element whoseluminance life is excellent is obtained.

The polymer compound according to the present invention may further havea constitutional unit represented by the following formula (2).

wherein Ar³ represents an unsubstituted or substituted arylene group, anunsubstituted or substituted divalent heterocyclic group, or a divalentgroup in which two or more same or different groups selected fromarylene groups and divalent heterocyclic groups are linked (the divalentgroup may have a substituent).

The polymer compound according to the present invention may have aconstitutional unit consisting of an unsubstituted or substitutedfluorenediyl group as the constitutional unit represented by the aboveformula (2).

The polymer compound according to the present invention may have aconstitutional unit consisting of an unsubstituted or substituted2,7-fluorenediyl group as the constitutional unit represented by theabove formula (2).

The polymer compound according to the present invention may have aconstitutional unit consisting of at least one group selected from thegroup consisting of an unsubstituted or substituted phenylene group, anunsubstituted or substituted naphthalenediyl group, an unsubstituted orsubstituted anthracenediyl group, and a group represented by thefollowing formula (3′) as the constitutional unit represented by theabove formula (2).

wherein a¹ and a² each independently represent an integer of 0 to 4; a³represents an integer of 0 to 5; R¹¹, R¹², and R¹³ each independentlyrepresent an unsubstituted or substituted alkyl group, an unsubstitutedor substituted alkoxy group, an unsubstituted or substituted aryl group,an unsubstituted or substituted aryloxy group, an unsubstituted orsubstituted monovalent heterocyclic group, an unsubstituted orsubstituted alkoxycarbonyl group, an unsubstituted or substituted silylgroup, a halogen atom, a carboxyl group, or a cyano group; and when R¹¹,R¹², R¹³, and R¹⁴ exist in plural, the plurality of R¹¹, R¹², R¹³, orR¹⁴ may be the same or different from each other.

The polymer compound according to the present invention may further havea constitutional unit represented by the following formula (4):

wherein b¹ and b² each independently represent 0 or 1; Ar⁴, Ar⁵, Ar⁶,and Ar⁷ each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or different groupsselected from arylene groups and divalent heterocyclic groups are linked(the group may have a substituent); R^(C), R^(D), and R^(E) eachindependently represent a hydrogen atom, an unsubstituted or substitutedalkyl group, an unsubstituted or substituted aryl group, or anunsubstituted or substituted monovalent heterocyclic group; Ar⁴, Ar⁵,Ar⁶, and Ar⁷ each may be linked to a group other than the group to forma ring structure, the other group being bonded to a nitrogen atom towhich the group is bonded; and the constitutional unit represented bythe formula (4) is different from the constitutional unit represented bythe formula (1).

As the constitutional unit represented by the above formula (4), thepolymer compound according to the present invention may have aconstitutional unit represented by the following formula (5):

wherein R^(F) represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; X¹represents a single bond, an oxygen atom, a sulfur atom, or a grouprepresented by —C(R¹⁴)₂— (R¹⁴ represents an unsubstituted or substitutedalkyl group or an unsubstituted or substituted aryl group; and aplurality of R¹⁴ may be the same or different from each other).

The polymer compound according to the present invention may have theconstitutional unit represented by the above formula (1), theconstitutional unit represented by the above formula (4), aconstitutional unit consisting of an unsubstituted or substitutedfluorenediyl group, and a constitutional unit consisting of anunsubstituted or substituted phenylene group.

The polymer compound according to the present invention may have theconstitutional unit represented by the above formula (1), theconstitutional unit represented by the above formula (4), aconstitutional unit consisting of an unsubstituted or substitutedfluorenediyl group, and a constitutional unit consisting of anunsubstituted or substituted naphthalenediyl group.

The polymer compound according to the present invention may have theconstitutional unit represented by the above formula (1), theconstitutional unit represented by the above formula (4), aconstitutional unit consisting of an unsubstituted or substitutedfluorenediyl group, and a constitutional unit consisting of anunsubstituted or substituted anthracenediyl group.

The polymer compound according to the present invention may have theconstitutional unit represented by the above formula (1), theconstitutional unit represented by the above formula (4), aconstitutional unit consisting of an unsubstituted or substitutedfluorenediyl group, and the constitutional unit represented by thefollowing formula (3) (namely, the constitutional unit including thegroup represented by the formula (3′)).

wherein a¹ and a² each independently represent an integer of 0 to 4; a³represents an integer of 0 to 5; R¹¹, R¹², and R¹³ each independentlyrepresent an unsubstituted or substituted alkyl group, an unsubstitutedor substituted alkoxy group, an unsubstituted or substituted aryl group,an unsubstituted or substituted aryloxy group, an unsubstituted orsubstituted monovalent heterocyclic group, an unsubstituted orsubstituted alkoxycarbonyl group, an unsubstituted or substituted silylgroup, a halogen atom, a carboxyl group, or a cyano group; and when R¹¹,R¹², R¹³, and R¹⁴ exist in plural, the plurality of R¹¹, R¹², R¹³, orR¹⁴ may be the same or different from each other.

In the polymer compound according to the present invention, n¹ and n² inthe above formula (1) each independently may be 3 or 4.

In the polymer compound according to the present invention, R^(A) andR^(B) in the above formula (1) each independently represent anunsubstituted or substituted aryl group or an unsubstituted orsubstituted monovalent heterocyclic group.

The polymer compound according to the present invention may besynthesized by condensation polymerization of a monomer (1) thatintroduces the constitutional unit represented by the above formula (1)with a monomer (X) that introduces a constitutional unit different fromthe constitutional unit, wherein when the number of the monomer (1) isN₁ and the number of the monomer (X) is N_(X), N₁ and N_(X) satisfy thefollowing formula (1). According to the polymer compound, alight-emitting element more excellent in luminance life is obtained.According to the polymer compound, a light-emitting device moreexcellent in luminance life is obtained.0.1≦N ₁×100/(N ₁ +N _(X))≦50  (I)

Moreover, the present invention provides a compound represented by thefollowing formula (1M):

wherein n¹ and n² each independently represent an integer of 1 to 5; R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ each independently represent ahydrogen atom, an unsubstituted or substituted alkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group,or an unsubstituted or substituted monovalent heterocyclic group; R^(A)and R^(B) each independently represent a hydrogen atom, an unsubstitutedor substituted alkyl group, an unsubstituted or substituted aryl group,or an unsubstituted or substituted monovalent heterocyclic group; Ar¹and Ar² each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or different groupsselected from arylene groups and divalent heterocyclic groups are linked(the group may have a substituent); when R², R³, and R⁴ exist in plural,the plurality of R¹, R², R³, or R⁴ may be the same or different fromeach other; among R¹, R², R³, and R⁴, adjacent groups may be linked toeach other to form a ring structure; among R⁷, R⁸, R⁹ and R¹⁰, adjacentgroups may be linked to each other to form a ring structure; Ar¹ andR^(A) may be linked to each other to form a ring structure; Ar² andR^(B) may be linked to each other to form a ring structure; and Z¹ andZ² each independently represent a group selected from the followingsubstituent group:<Substituent Group>

a chlorine atom, a bromine atom, iodine atom, a group represented by—O—S(═O)₂R⁴¹ wherein R⁴¹ represents an alkyl group, or an aryl groupthat may be substituted with an alkyl group, an alkoxy group, a nitrogroup, a fluorine atom, or a cyano group, a group represented by—B(OR⁴²)₂ wherein R⁴² represents a hydrogen atom or an alkyl group; anda plurality of R⁴² present may be the same or different from each otherand may be bonded to each other to form a cyclic structure, a grouprepresented by —BF₄Q¹ wherein Q¹ represents a monovalent cation selectedfrom the group consisting of Li⁺, Na⁺, K⁺, Rb⁺, and Cs⁺, a grouprepresented by —MgY¹ wherein Y¹ represents a chlorine atom, a bromineatom, or an iodine atom, a group represented by —ZnY² wherein Y²represents a chlorine atom, a bromine atom, or an iodine atom, and agroup represented by —Sn(R⁴³)₃ wherein R⁴³ represents a hydrogen atom oran alkyl group; and a plurality of R⁴³ present may be the same ordifferent from each other and may be bonded to each other to form acyclic structure.

Moreover, the present invention provides a composition containing thepolymer compound according to the present invention and at least oneselected from the group consisting of a hole transport material, anelectron transport material, and a light-emitting material. Thecomposition can be suitably used in production of the light-emittingdevice, and the light-emitting device to be obtained is excellent inluminance life.

The composition according to the present invention may contain a tripletlight-emitting complex as the light-emitting material. The compositioncan be suitably used in production of the light-emitting device, and thelight-emitting device to be obtained is excellent in luminance life.

Moreover, the present invention provides a liquid composition containingthe polymer compound according to the present invention and a solvent.According to the liquid composition, an organic film containing thepolymer compound can be easily produced.

Moreover, the present invention provides an organic film containing thepolymer compound according to the present invention. The organic film isuseful for production of the light-emitting device whose luminance lifeis excellent.

Moreover, the present invention provides an organic film using thecomposition according to the present invention. The organic film isuseful for production of the light-emitting device whose luminance lifeis excellent.

Moreover, the present invention provides a light-emitting device havingthe organic film according to the present invention. The light-emittingdevice is excellent in luminance life.

Moreover, the present invention provides a surface lighting source and adisplay device having the light-emitting device according to the presentinvention.

Advantageous Effects of Invention

According to the present invention, a polymer compound useful forproduction of a light-emitting device whose luminance life is excellentcan be provided. Moreover, according to the present invention, acomposition, liquid composition, organic film, light-emitting device,surface lighting source, and display device containing the polymercompound can be provided. Further, according to the present invention, araw material compound for the polymer compound can be provided.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic sectional view showing one embodiment of alight-emitting device according to the present invention.

FIG. 2 is a schematic sectional view showing another embodiment of alight-emitting device according to the present invention.

FIG. 3 is a schematic sectional view showing one embodiment of a surfacelighting source according to the present invention.

DESCRIPTION OF EMBODIMENTS

Hereinafter, terms commonly used herein will be described, usingexamples when necessary.

Herein, “Me” represents a methyl group, “Et” represents an ethyl group,“Ph” represents a phenyl group, and “t-Bu” represents a tert-butylgroup.

The “constitutional unit” means one or more unit structures that arepresent in the polymer compound. It is preferable that the“constitutional unit” be included in the polymer compound as a“repeating unit” (namely, two or more unit structures that are presentin the polymer compound).

The term “C_(x) to C_(y)” (x and y are a positive integer that satisfiesx<y) means that the number of carbon atoms in a partial structurecorresponding to the name of the functional group written immediatelyafter the term is x to y. Namely, in the case where the organic groupwritten immediately after “C_(x) to C_(y)” is an organic group named incombination of a plurality of names of functional groups (for example, aC_(x) to C_(y) alkoxyphenyl group), the term means that among theplurality of names of functional groups, the number of carbon atoms inthe partial structure corresponding to the name of the functional groupwritten immediately after “C_(x) to C_(y)” (for example, alkoxy) is x toy. For example, the “C₁ to C₁₂ alkyl group” means an alkyl group having1 to 12 carbon atoms, and the “C₁ to C₁₂ alkoxyphenyl group” means aphenyl group having an “alkoxy group having 1 to 12 carbon atoms.”

Herein, the term “unsubstituted or substituted” means that thefunctional group written immediately after the term may have asubstituent. For example, the “unsubstituted or substituted alkyl group”means an “unsubstituted alkyl group or an alkyl group having asubstituent.”

Examples of the substituent include an alkyl group, an alkoxy group, analkylthio group, an aryl group, an acyloxy group, an arylthio group, analkenyl group, an alkynyl group, an amino group, a silyl group, halogenatoms, an acyl group, an acyloxy group, an oxycarbonyl group, amonovalent heterocyclic group, a heterocycleoxy group, a heterocyclethiogroup, imine residues, amide compound residues, acid imide residues, acarboxyl group, a hydroxy group, a nitro group, and a cyano group. Thesegroups may further have a substituent selected from the groups above.

The “alkyl group” may have a substituent, and may be any of a linearalkyl group, a branched alkyl group, and a cyclic alkyl group(cycloalkyl group). Unless otherwise specified, without including thenumber of carbon atoms of the substituent, the number of carbon atoms ofthe alkyl group is preferably 1 to 20, more preferably 1 to 15, andstill more preferably 1 to 12 in the linear alkyl group and the branchedalkyl group; without including the number of carbon atoms of thesubstituent, the number of carbon atoms of the alkyl group is preferably3 to 20, more preferably 3 to 15, and still more preferably 3 to 12 inthe cyclic alkyl group. Examples of the alkyl group include a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an isoamyl group, a hexyl group, a cyclohexyl group, aheptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, adecyl group, a 3,7-dimethyloctyl group, and a dodecyl group.

The “alkoxy group” may have a substituent, and may be any of a linearalkoxy group, a branched alkoxy group, and a cyclic alkoxy group(cycloalkoxy group). Unless otherwise specified, without including thenumber of carbon atoms of the substituent, the number of carbon atoms ofthe alkoxy group is preferably 1 to 20, more preferably 1 to 15, andstill more preferably 1 to 12 in the linear alkoxy group and thebranched alkoxy group; without including the number of carbon atoms ofthe substituent, the number of carbon atoms of the alkoxy group ispreferably 3 to 20, more preferably 3 to 15, and still more preferably 3to 12 in the cyclic alkoxy group. Examples of the alkoxy group include amethoxy group, ethoxy group, a propyloxy group, an isopropyloxy group, abutoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxygroup, a pentyloxy group, a hexyloxy group, a cyclohexyloxy group, aheptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxygroup, a decyloxy group, a 3,7-dimethyloctyloxy group, and a dodecyloxygroup.

The “alkylthio group” may have a substituent, and may be any of a linearalkylthio group, a chain alkylthio group, and a cyclic alkylthio group(cycloalkylthio group). Unless otherwise specified, without includingthe number of carbon atoms of the substituent, the number of carbonatoms of the alkoxy group is preferably 1 to 20, more preferably 1 to15, and still more preferably 1 to 12 in the linear alkylthio group andthe branched alkylthio group; without including the number of carbonatoms of the substituent, the number of carbon atoms of the alkoxy groupis preferably 3 to 20, more preferably 3 to 15, and still morepreferably 3 to 12 in the cyclic alkylthio group. Examples of thealkylthio group include a methylthio group, an ethylthio group, apropylthio group, an isopropylthio group, a butylthio group, anisobutylthio group, a sec-butylthio group, a tert-butylthio group, apentylthio group, a hexylthio group, a cyclohexylthio group, aheptylthio group, an octylthio group, a 2-ethylhexylthio group, anonylthio group, a decylthio group, a 3,7-dimethyloctylthio group, and adodecylthio group.

The “aryl group” is the remaining atomic group in which one hydrogenatom bonded to carbon atoms that form an aromatic ring is removed froman aromatic hydrocarbon. The aryl group may have a substituent, andexamples of the aryl group include those having a benzene ring, andthose having a condensation ring. Unless otherwise specified, withoutincluding the number of carbon atoms of the substituent, the number ofcarbon atoms of the aryl group is preferably 6 to 60, more preferably 6to 48, and still more preferably 6 to 30. Examples of the aromatichydrocarbon include benzene, naphthalene, anthracene, phenanthrene,naphthacene, fluorene, pyrene, and perylene. Examples of the aryl groupinclude a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, and2-fluorenyl group.

The “aryloxy group” is the group represented by —O—Ar¹¹ (Ar¹¹ representsthe aryl group), and the aryl group in Ar¹¹ may have a substituent.Unless otherwise specified, without including the number of carbon atomsof the substituent, the number of carbon atoms of the aryloxy group ispreferably 6 to 60, more preferably 6 to 48, and still more preferably 6to 30. Examples of the aryloxy group include a phenoxy group, a1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a2-anthracenyloxy group, a 9-anthracenyloxy group, and a 2-fluorenyloxygroup.

The “arylthio group” is the group represented by —S—Ar¹² (Ar¹²represents the aryl group), and the aryl group in Ar¹² may have asubstituent. Unless otherwise specified, without including the number ofcarbon atoms of the substituent, the number of carbon atoms of thearylthio group is preferably 6 to 60, more preferably 6 to 48, and stillmore preferably 6 to 30. Examples of the arylthio group include aphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, a1-anthracenylthio group, a 2-anthracenylthio group, a 9-anthracenylthiogroup, and a 2-fluorenylthio group.

The “alkenyl group” is the remaining atomic group in which one hydrogenatom bonded to sp² carbon atoms in alkene is removed. The alkenyl groupmay have a substituent, and may be any of a linear alkenyl group, abranched alkenyl group, and a cyclic alkenyl group. Unless otherwisespecified, without including the number of carbon atoms of thesubstituent, the number of carbon atoms of the alkenyl group ispreferably 2 to 20, more preferably 2 to 15, and still more preferably 2to 10 in the linear alkenyl group and the branched alkenyl group;without including the number of carbon atoms of the substituent, thenumber of carbon atoms of the alkenyl group is preferably 3 to 20, morepreferably 4 to 15, and still more preferably 5 to 10 in the cyclicalkenyl group. Examples of the alkenyl group include a vinyl group, a1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenylgroup, a 1-pentenyl group, a 2-pentenyl group, a 1-hexenyl group, a2-hexenyl group, and a 1-octenyl group.

The “alkynyl group” is the remaining atomic group in which one hydrogenatom bonded to sp¹ carbon atoms in alkyne is removed. The alkynyl groupmay have a substituent, and may be any of a linear alkynyl group, abranched alkynyl group, and a cyclic alkynyl group. Unless otherwisespecified, without including the number of carbon atoms of thesubstituent, the number of carbon atoms of the alkynyl group ispreferably 2 to 20, more preferably 2 to 15, and still more preferably 2to 10 in the linear alkynyl group and the branched alkynyl group;without including the number of carbon atoms of the substituent, thenumber of carbon atoms of the alkynyl group is preferably 5 to 20, morepreferably 6 to 15, and still more preferably 7 to 10 in the cyclicalkynyl group. Examples of the alkynyl group include an ethynyl group, a1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynylgroup, a 1-pentynyl group, a 2-pentynyl group, a 1-hexynyl group, a2-hexynyl group, and a 1-octynyl group.

The “amino group” may have a substituent, and is preferably anunsubstituted amino group and an amino group in which one or twohydrogens atom that the alkyl group has is substituted with one or twosubstituents selected from an alkyl group, an aryl group, an arylalkylgroup, and a monovalent heterocyclic group (hereinafter, referred to asa “substituted amino group”). The substituent may further have asubstituent (hereinafter, a substituent that a substituent having anorganic group further has is referred to as a “secondary substituent” insome cases). Without including the number of carbon atoms of thesecondary substituent, the number of carbon atoms of the substitutedamino group is preferably 1 to 60, more preferably 2 to 48, and stillmore preferably 2 to 40.

Examples of the substituted amino group include a methylamino group, adimethylamino group, an ethylamino group, a diethylamino group, apropylamino group, a dipropylamino group, an isopropylamino group, adiisopropylamino group, a butylamino group, an isobutylamino group, asec-butylamino group, a tert-butylamino group, a pentylamino group, ahexylamino group, a heptylamino group, an octylamino group, a2-ethylhexylamino group, a nonylamino group, a decylamino group, a3,7-dimethyloctylamino group, a dodecylamino group, a cyclopentylaminogroup, a dicyclopentylamino group, a cyclohexylamino group, adicyclohexylamino group, a ditrifluoromethylamino group, a phenylaminogroup, a diphenylamino group, a C₁ to C₁₂ alkoxyphenylamino group, abis(C₁ to C₁₂ alkoxyphenyl)amino group, a C₁ to C₁₂ alkylphenylaminogroup, a bis(C₁ to C₁₂ alkylphenyl)amino group, a 1-naphthylamino group,a 2-naphthylamino group, a pentafluorophenylamino group, a pyridylaminogroup, a pyridazinylamino group, a pyrimidinylamino group, apyrazinylamino group, a triazinylamino group, a phenyl-C₁ to C₁₂alkylamino group, a C₁ to C₁₂ alkoxyphenyl-C₁ to C₁₂ alkylamino group, adi(C₁ to C₁₂ alkoxyphenyl-C₁ to C₁₂ alkyl)amino group, a C₁ to C₁₂alkylphenyl-C₁ to C₁₂ alkylamino group, a di(C₁ to C₁₂ alkylphenyl-C₁ toC₁₂ alkyl)amino group, a 1-naphthyl-C₁ to C₁₂ alkylamino group, and a2-naphthyl-C₁ to C₁₂ alkylamino group.

The “silyl group” may have a substituent, and is preferably anunsubstituted silyl group and a silyl group in which one to threehydrogen atoms that the silyl group has is substituted with one to threesubstituents selected from an alkyl group, an aryl group, an arylalkylgroup, and a monovalent heterocyclic group (hereinafter, referred to asa “substituted silyl group”). The substituent may have a secondarysubstituent. Without including the number of carbon atoms of thesecondary substituent, the number of carbon atoms of the substitutedsilyl group is preferably 1 to 60, more preferably 3 to 48, and stillmore preferably 3 to 40.

Examples of the substituted silyl group include a trimethylsilyl group,a triethylsilyl group, a tripropylsilyl group, a tri-isopropylsilylgroup, a dimethyl-isopropylsilyl group, a diethyl-isopropylsilyl group,a tert-butyldimethylsilyl group, a pentyldimethylsilyl group, ahexyldimethylsilyl group, a heptyldimethylsilyl group, anoctyldimethylsilyl group, a 2-ethylhexyl-dimethylsilyl group, anonyldimethylsilyl group, a decyldimethylsilyl group, a3,7-dimethyloctyl-dimethylsilyl group, a dodecyldimethylsilyl group, aphenyl-C₁ to C₁₂ alkylsilyl group, a C₁ to C₁₂ alkoxyphenyl-C₁ to C₁₂alkylsilyl group, a C₁ to C₁₂ alkylphenyl-C₁ to C₁₂ alkylsilyl group, a1-naphthyl-C₁ to C₁₂ alkylsilyl group, a 2-naphthyl-C₁ to C₁₂ alkylsilylgroup, a phenyl-C₁ to C₁₂ alkyldimethylsilyl group, a triphenylsilylgroup, a tri-p-xylylsilyl group, a tribenzylsilyl group, adiphenylmethylsilyl group, a tert-butyldiphenylsilyl group, and adimethylphenylsilyl group.

Examples of the “acyl group” include groups represented by —C(═O)—R⁴⁴(R⁴⁴ represents the alkyl group, the aryl group, or a monovalentheterocyclic group described later). The alkyl group, the aryl group,and the monovalent heterocyclic group in R⁴⁴ may have a substituent.Unless otherwise specified, without including the number of carbon atomsof the substituent, the number of carbon atoms of the acyl group ispreferably 2 to 20, more preferably 2 to 18, and still more preferably 2to 16. Examples of the acyl group include an acetyl group, a propionylgroup, a butyryl group, an isobutyryl group, a pivaloyl group, and abenzoyl group. Examples of the acyl group having a substituent includean acyl group having a halogen atom as a substituent (such as atrifluoroacetyl group and a pentafluorobenzoyl group).

Examples of the “acyloxy group” include groups represented by—O—C(═O)—R⁴⁵ (R⁴⁵ represents the alkyl group, the aryl group, or amonovalent heterocyclic group described later). The alkyl group, thearyl group, and the monovalent heterocyclic group in R⁴⁵ may have asubstituent. Unless otherwise specified, without including the number ofcarbon atoms of the substituent, the number of carbon atoms of theacyloxy group is preferably 2 to 20, more preferably 2 to 18, and stillmore preferably 2 to 16. Examples of the acyloxy group include anacetoxy group, a propionyloxy group, a butyryloxy group, anisobutyryloxy group, a pivaloyloxy group, and a benzoyloxy group.Examples of the acyloxy group having a substituent include an acyloxygroup having a halogen atom as a substituent (such as atrifluoroacetyloxy group and a pentafluorobenzoyloxy group).

Examples of the “oxycarbonyl group” include groups represented by—C(═O)—O—R^(45a) (R^(45a) represents the alkyl group, the aryl group, ora monovalent heterocyclic group described later). The alkyl group, thearyl group, and the monovalent heterocyclic group in R^(45a) may have asubstituent. Unless otherwise specified, without including the number ofcarbon atoms of the substituent, the number of carbon atoms of theoxycarbonyl group is preferably 2 to 20, more preferably 2 to 18, andstill more preferably 2 to 16.

The “monovalent heterocyclic group” is the remaining atomic group inwhich one hydrogen atom is removed from a heterocyclic compound. Themonovalent heterocyclic group may have a substituent, and examples ofthe monovalent heterocyclic group include a monocyclic group, and agroup having a condensation ring. Unless otherwise specified, withoutincluding the number of carbon atoms of the substituent, the number ofcarbon atoms in the monovalent heterocyclic group is preferably 4 to 60,more preferably 4 to 30, and still more preferably 4 to 20.

The heterocyclic compound designates compounds among organic compoundshaving a cyclic structure and the compounds including not only a carbonatom but also a hetero atom such as an oxygen atom, a sulfur atom, anitrogen atom, a phosphorus atom, a boron atom, a silicon atom, aselenium atom, a tellurium atom, and an arsenic atom as the device thatforms the ring.

As the monovalent heterocyclic group, monovalent aromatic heterocyclicgroups are preferable. The monovalent aromatic heterocyclic group is theremaining atomic group in which one hydrogen atom is removed from anaromatic heterocyclic compound. Examples of the aromatic heterocycliccompound include compounds in which a heterocyclic ring itselfcontaining a hetero atom demonstrates aromaticity, such as oxadiazole,thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan,pyridine, pyrazine, pyrimidine, triazine, pyridazin, quinoline,isoquinoline, carbazole, dibenzophosphole, dibenzofuran, anddibenzothiophene; and compounds in which a heterocyclic ring itselfcontaining a hetero atom does not demonstrate aromaticity, but anaromatic ring is fused to the heterocycle, such as phenoxazine,phenothiazine, dibenzoborole, dibenzosilole, and benzopyran.

The “heterocycleoxy group” is a group represented by —O—Ar¹³ (Ar¹³represents the monovalent heterocyclic group), and the monovalentheterocyclic group in Ar¹³ may have a substituent. Unless otherwisespecified, without including the number of carbon atoms of thesubstituent, the number of carbon atoms of the heterocycleoxy group ispreferably 4 to 60, more preferably 4 to 30, and still more preferably 4to 20. Examples of the heterocycleoxy group include a pyridyloxy group,a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group,and a triazinyloxy group.

The “heterocyclethio group” is a group represented by —S—Ar¹⁴ (Ar¹⁴represents the monovalent heterocyclic group), and the monovalentheterocyclic group in Ar¹⁴ may have a substituent. Unless otherwisespecified, without including the number of carbon atoms of thesubstituent, the number of carbon atoms of the heterocyclethio group ispreferably 4 to 60, more preferably 4 to 30, and still more preferably 4to 20. Examples of the heterocyclethio group include a pyridylthiogroup, a pyridazinylthio group, a pyrimidinylthio group, a pyrazinylthiogroup, and a triazinylthio group.

The “imine residue” means a residue in which a hydrogen atom in theformula is removed from an imine compound having a structure representedby at least one of the formula: H—N═C(R⁴⁶)₂ and the formula:H—C(R⁴⁷)═N—R⁴⁸. In the formulas, R⁴⁶, R⁴⁷, and R⁴⁸ each independentlyrepresent the alkyl group, the aryl group, the alkenyl group, thealkynyl group, or the monovalent heterocyclic group. The alkyl group,the aryl group, the alkenyl group, the alkynyl group, and the monovalentheterocyclic group in R⁴⁶, R⁴⁷ and R⁴⁸ may have a substituent. Aplurality of R⁴⁶ present may be the same or different from each other,or may be linked to each other to form a cyclic structure. Examples ofthe imine residue include groups represented by the following structure:

The “amide compound residue” means a residue in which a hydrogen atom inthe formula is removed from an amide compound having a structurerepresented by at least one of the formula: H—N(R⁴⁹)—C(═O)R⁵⁰ and theformula: H—C(═O)—N(R⁵¹)₂. In the formulas, R⁴⁹, R⁵⁰, and R⁵¹ eachindependently represent the alkyl group, the aryl group, the alkenylgroup, the alkynyl group, or the monovalent heterocyclic group. Thealkyl group, the aryl group, the alkenyl group, the alkynyl group, andthe monovalent heterocyclic group in R⁴⁹, R⁵⁰, and R⁵¹ may have asubstituent. A plurality of R⁵¹ present may be the same or differentfrom each other, and may be linked to each other to form a cyclicstructure. Examples of the amide compound residue include formamideresidues, acetoamide residues, propioamide residues, butyroamideresidues, benzamide residues, trifluoroacetoamide residues,pentafluorobenzamide residues, diformamide residues, diacetoamideresidues, dipropioamide residues, dibutyroamide residues, dibenzamideresidues, ditrifluoroacetoamide residues, and dipentafluorobenzamideresidues.

The “acid imide residue” means a residue obtained by removing onehydrogen atom bonded to a nitrogen atom from an acid imide. The numberof carbon atoms of the acid imide residue is preferably 4 to 20, morepreferably 4 to 18, and still more preferably 4 to 16. Examples of theacid imide residue include groups represented by the followingstructure:

Examples of the “unsubstituted or substituted alkyl group” includeunsubstituted alkyl groups and the alkyl groups having substituentsabove. Here, the substituent that the alkyl group has is preferably asubstituent selected from an alkoxy group, an aryl group, an aryloxygroup, a monovalent heterocyclic group, a heterocycleoxy group, and ahalogen atom, unless otherwise specified.

Examples of the “unsubstituted or substituted alkoxy group” includeunsubstituted alkoxy groups and the alkoxy groups having substituentsabove. Here, the substituent that the alkoxy group has is preferably asubstituent selected from an alkoxy group, an aryl group, an aryloxygroup, a monovalent heterocyclic group, a heterocycleoxy group, and ahalogen atom, unless otherwise specified.

Examples of the “unsubstituted or substituted aryl group” includeunsubstituted aryl groups and the aryl groups having the substituents.Here, the substituent that the aryl group has is preferably asubstituent selected from an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, a monovalent heterocyclic group, aheterocycleoxy group, and a halogen atom unless otherwise specified.

Examples of the “unsubstituted or substituted aryloxy group” includeunsubstituted aryloxy groups and aryloxy groups having the substituentsabove. Here, the substituent that the aryloxy group has is preferably asubstituent selected from an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, a monovalent heterocyclic group, aheterocycleoxy group, and a halogen atom unless otherwise specified.

Examples of the “unsubstituted or substituted monovalent heterocyclicgroup” include unsubstituted monovalent heterocyclic groups andmonovalent heterocyclic groups having the substituents above. Here, thesubstituent that the monovalent heterocyclic group has is preferably asubstituent selected from an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, a monovalent heterocyclic group, aheterocycleoxy group, and a halogen atom unless otherwise specified.

Examples of the “unsubstituted or substituted arylene group” includeunsubstituted arylene groups and arylene groups having the substituentsabove. Here, the substituent that the arylene group has is preferably asubstituent selected from an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, a monovalent heterocyclic group, aheterocycleoxy group and a halogen atom unless otherwise specified.

The “arylene group” is the remaining atomic group in which two hydrogenatoms bonded to carbon atoms that form an aromatic ring are removed froman aromatic hydrocarbon. The arylene group may have a substituent, andgroups having a benzene ring and groups having a condensation ring areincluded in the arylene group. Unless otherwise specified, withoutincluding the number of carbon atoms of the substituent, the number ofcarbon atoms of the arylene group is preferably 6 to 60, more preferably6 to 48, and still more preferably 6 to 30.

Examples of the aromatic hydrocarbon include benzene, naphthalene,anthracene, phenanthrene, naphthacene, fluorene, pyrene, and perylene.Examples of the arylene group include phenylene groups such as a1,4-phenylene group, a 1,3-phenylene group, and a 1,2-phenylene group;naphthalenediyl groups such as a 1,4-naphthalenediyl group, a1,5-naphthalenediyl group, 2,6-naphthalenediyl group, and a2,7-naphthalenediyl; anthracenediyl groups such as a 1,4-anthracenediylgroup, a 1,5-anthracenediyl group, a 2,6-anthracenediyl group, and a9,10-anthracenediyl group; phenanthrenediyl groups such as a2,7-phenanthrenediyl group; naphthacenediyl groups such as a1,7-naphthacenediyl group, a 2,8-naphthacenediyl group, and a5,12-naphthacenediyl group; fluorenediyl groups such as a2,7-fluorenediyl group and a 3,6-fluorenediyl group; pyrenediyl groupssuch as a 1,6-pyrenediyl group, a 1,8-pyrenediyl group, a 2,7-pyrenediylgroup, and a 4,9-pyrenediyl group; and perylenediyl groups such as a3,8-perylenediyl group, a 3,9-perylenediyl group, and a3,10-perylenediyl group.

Examples of the “unsubstituted or substituted divalent heterocyclicgroup” include unsubstituted divalent heterocyclic groups and divalentheterocyclic groups having the substituents above. Here, the substituentthat the divalent heterocyclic group has is preferably a substituentselected from an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, a monovalent heterocyclic group, a heterocycleoxy group, and ahalogen atom unless otherwise specified.

The “divalent heterocyclic group” is the remaining atomic group in whichtwo hydrogen atoms are removed from a heterocyclic compound. Thedivalent heterocyclic group may have a substituent, and monocyclicgroups and groups having a condensation ring are included in thedivalent heterocyclic group. Unless otherwise specified, withoutincluding the number of carbon atoms of the substituent, the number ofcarbon atoms of the divalent heterocyclic group is preferably 4 to 60,more preferably 4 to 30, and still more preferably 4 to 20.

As the divalent heterocyclic group, divalent aromatic heterocyclicgroups are preferable. The divalent aromatic heterocyclic group is theremaining atomic group in which two hydrogen atoms are removed from anaromatic heterocyclic compound.

Examples of the divalent heterocyclic group include pyridinediyl groupssuch as a 2,5-pyridinediyl group and a 2,6-pyridinediyl group;quinolinediyl groups such as a 2,6-quinolinediyl group; isoquinolinediylgroups such as a 1,4-isoquinolinediyl group and a 1,5-isoquinolinediylgroup; quinoxalinediyl groups such as a 5,8-quinoxalinediyl group;2,1,3-benzothiadiazole groups such as a 2,1,3-benzothiadiazole-4,7-diylgroup; benzothiazolediyl groups such as a 4,7-benzothiazolediyl group;dibenzosilolediyl groups such as a 2,7-dibenzosilolediyl group;dibenzofurandiyl groups such as a dibenzofuran-4,7-diyl group and adibenzofuran-3,8-diyl group; and dibenzothiophenediyl groups such as adibenzothiophene-4,7-diyl group and a dibenzothiophene-3,8-diyl group.

Examples of the “divalent group in which two or more same or differentgroups selected from arylene groups and divalent heterocyclic groups arelinked” include divalent groups in which two groups selected fromarylene groups and divalent heterocyclic groups are linked with a singlebond such as a 2,7-biphenylylene group and a 3,6-biphenylylene group.The divalent group may have a substituent, and the substituent that thedivalent group has is preferably a substituent selected from an alkylgroup, an alkoxy group, an aryl group, an aryloxy group, a monovalentheterocyclic group, a heterocycleoxy group, and a halogen atom unlessotherwise specified.

Hereinafter, suitable embodiments of the polymer compound, compound,composition, liquid composition, organic film, light-emitting device,surface lighting source, and display device according to the presentinvention will be described in detail.

(Polymer Compound)

The polymer compound according to the present embodiment has a firstconstitutional unit represented by the following formula (1). Thepolymer compound is useful in production of the light-emitting devicewhose luminance life is excellent because the polymer compound has thisconstitutional unit.

It is preferable that the polymer compound according to the presentembodiment be a conjugated polymer compound. The polymer compoundaccording to the present embodiment may further have a secondconstitutional unit represented by the following formula (2) and/or athird constitutional unit represented by the following formula (4). Sucha polymer compound is more useful in production of the light-emittingdevice whose luminance life is excellent. Here, the “conjugated polymercompound” is a polymer compound in which a conjugated system expands onthe main chain skeleton, and examples thereof include polyaryleneshaving an arylene group such as polyfluorene and polyphenylene as aconstitutional unit; polyheteroarylene having a divalent heterocyclicgroup such as polythiophene and polydibenzofuran as a constitutionalunit; polyarylenevinylene such as polyphenylenevinylene; and copolymershaving these constitutional units in combination. The “conjugatedpolymer compound” may be a compound substantially conjugated even if ahetero atom or the like is included in the main chain in theconstitutional unit; for example, the “conjugated polymer compound” mayinclude a constitutional unit derived from triarylamine as theconstitutional unit.

Hereinafter, the first constitutional unit, the second constitutionalunit, and the third constitutional unit each will be described indetail.

(First Constitutional Unit)

The first constitutional unit is the constitutional unit represented bythe following formula (1):

wherein n¹ and n² each independently represent an integer of 1 to 5; R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ each independently represent ahydrogen atom, an unsubstituted or substituted alkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group,or an unsubstituted or substituted monovalent heterocyclic group; R^(A)and R^(B) each independently represent a hydrogen atom, an unsubstitutedor substituted alkyl group, an unsubstituted or substituted aryl group,or an unsubstituted or substituted monovalent heterocyclic group; Ar¹and Ar² each independently represent an “unsubstituted or substitutedarylene group,” an “unsubstituted or substituted divalent heterocyclicgroup,” or a “divalent group in which two or more same or differentgroups selected from arylene groups and divalent heterocyclic groups arelinked (the group may have a substituent).”

As R¹, R², R³, and R⁴, the hydrogen atom, the unsubstituted orsubstituted alkyl group, or the unsubstituted or substituted aryl groupare preferable, or the hydrogen atom and the unsubstituted orsubstituted alkyl group are more preferable because synthesis of themonomer is easy, and the luminance life of the light-emitting device tobe obtained is more excellent in the case where the polymer compound isused in production of the light-emitting device.

In the formula (1), when n¹ is an integer of 2 to 5, a plurality of R¹present may be the same or different from each other, and a plurality ofR² present may be the same or different from each other. When n² is aninteger of 2 to 5, a plurality of R³ present may be the same ordifferent from each other, and a plurality of R⁴ present may be the sameor different from each other.

Among R¹, R², R³, and R⁴, adjacent groups may be linked to each other toform a cyclic structure. Among R⁷, R⁸, R⁹, and R¹⁰, adjacent groups maybe linked to each other to form a cyclic structure.

Ar¹ and R^(A) may be linked to each other to form a ring structure. Ar²and R^(B) may be linked to each other to form a ring structure. Here,the expression “may be linked to each other to form a ring structure”indicates that Ar¹ and R^(A) (or Ar² and R^(B)) may be bonded with asingle bond or a group represented by —O—, —S—, —C(═O)—, —C(═O)—O—,—N(R¹⁵)—, —C(═O)—N(R¹⁵)—, or —C(R¹⁵)₂— (R¹⁵ represents an unsubstitutedor substituted alkyl group or an unsubstituted or substituted arylgroup; when R¹⁵ exists in plural, the plurality of R¹⁵ may be the sameor different from each other), to form a ring structure. Thereby,usually a 5- to 7-membered ring is formed.

It is preferable that the content of the first constitutional unit be0.1 to 70 mol % of the total constitutional units, it is more preferablethat the content of the first constitutional unit be 0.1 to 50 mol % ofthe total constitutional units, and it is still more preferable that thecontent of the first constitutional unit be 0.1 to 40 mol % of the totalconstitutional units because the luminance life of the light-emittingdevice to be obtained is more excellent in the case where the polymercompound is used in production of the light-emitting device.

In the first constitutional unit, for example, stereoisomerism can beproduced when n¹ and/or n² is 2 or more and the first constitutionalunit has a substituent, when R¹ and R² are different from each other,and when R³ and R⁴ are different from each other. As the firstconstitutional unit, the polymer compound may have only a constitutionalunit having the same stereoisomerism, or may have a plurality ofconstitutional units having stereoisomerism different from each other.Examples of the stereoisomerism include diastereoisomers andenantiomers.

In the case where the dihydrophenanthrene skeleton portion of the firstconstitutional unit is represented by the formula (1-A), examples of thestereoisomerism are represented by the following formula (1-a), theformula (1-b), the formula (1-c), and the formula (1-d). In thefollowing formulas, R^(a) and R^(b) each independently represent analkyl group.

The constitutional unit represented by the formula (1-a), theconstitutional unit represented by the formula (1-b), the constitutionalunit represented by the formula (1-c) and the constitutional unitrepresented by the formula (1-d) are in the relationship ofdiastereoisomers.

In the formula (1), in the case where the group represented by R¹, R²,R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ has a substituent, the substituentis preferably an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, and a cyano group, more preferably analkyl group, an alkoxy group, an aryl group, an aryloxy group, anarylalkyl group, an arylalkoxy group, a substituted amino group, an acylgroup, and a cyano group, and still more preferably an alkyl group, analkoxy group, and an aryl group.

In the formula (1), R¹, R², R³, and R⁴ can be a hydrogen atom, anunsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group. Here, as the substituted alkyl group in R¹, R²,R³, and R⁴, an arylalkyl group or an alkylarylalkyl group can beselected; as the substituted aryl group in R¹, R², R³, and R⁴, analkylaryl group can be selected.

In the formula (1), R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ can be a hydrogen atom,an unsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group. Here, as the substituted alkyl group in R⁵, R⁶,R⁷, R⁸, R⁹, and R¹⁰, an arylalkyl group or an alkylarylalkyl group canbe selected; as the substituted aryl group in R⁵, R⁶, R⁷, R⁸, R⁹, andR¹⁰, an alkylaryl group can be selected.

It is preferable that R^(A) and R^(B) be a substituted alkyl group, anunsubstituted or substituted aryl group, or an unsubstituted orsubstituted monovalent heterocyclic group; it is more preferable thatR^(A) and R^(B) be an unsubstituted or substituted aryl group, or anunsubstituted or substituted monovalent heterocyclic group; and it isstill more preferable that R^(A) and R^(B) be an unsubstituted orsubstituted aryl group because the stability of the polymer compoundaccording to the present embodiment is good and the luminance life ofthe light-emitting device using the polymer compound is more excellent.

As R⁵, R⁶, R⁷, and R¹⁰, a hydrogen atom, an unsubstituted or substitutedalkyl group, and an unsubstituted or substituted aryl group arepreferable, and it is more preferable that at least two be a hydrogenatom because synthesis of the monomer is easy and the luminance life ofthe light-emitting device using the polymer compound is more excellent.

As R⁸ and R⁹, a hydrogen atom, an unsubstituted or substituted alkylgroup, and an unsubstituted or substituted aryl group are preferable,and a hydrogen atom and an unsubstituted or substituted alkyl group aremore preferable because the luminance life of the light-emitting deviceto be obtained is more excellent in the case where the polymer compoundis used in production of the light-emitting device.

In the case where the group represented by R^(A) and R^(B) has asubstituent in the formula (1), the substituent is preferably an alkylgroup, an alkoxy group, an aryl group, an aryloxy group, an arylalkylgroup, an arylalkoxy group, an arylalkenyl group, an arylalkynyl group,an amino group, a substituted amino group, a halogen atom, an acylgroup, an acyloxy group, a monovalent heterocyclic group, a carboxylgroup, a nitro group, and a cyano group, more preferably an alkyl group,an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, an acyl group, and a cyanogroup, and still more preferably an alkyl group, an alkoxy group, and anaryl group.

In the formula (1), the alkyl group in R^(A) and R^(B) is the same asthe “alkyl group” described as the term commonly used; the alkyl groupis preferably a C₁ to C₂₀ alkyl group. The alkyl group may have asubstituent.

In the formula (1), the aryl group in R^(A) and R^(B) is the same “arylgroup” described as the term commonly used; the aryl group is preferablya phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenylgroup, a 2-anthracenyl group, a 9-anthracenyl group, and a 2-fluorenyl.The aryl group may have a substituent.

In the formula (1), the monovalent heterocyclic group in R^(A) and R^(B)is the same “monovalent heterocyclic group” described as the termcommonly used; the monovalent heterocyclic group is preferably a pyridylgroup, a pyrimidyl group, a triazyl group, and a quinolyl group. Themonovalent heterocyclic group may have a substituent.

In the case where the group represented by Ar¹ and Ar² has a substituentin the formula (1), examples of the substituent include an alkyl group,an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, an arylalkenyl group, an arylalkynyl group, an aminogroup, a substituted amino group, a halogen atom, an acyl group, anacyloxy group, a monovalent heterocyclic group, a carboxyl group, anitro group, and a cyano group; the group is preferably an alkyl group,an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, an acyl group, and a cyanogroup, and more preferably an alkyl group, an alkoxy group, and an arylgroup.

In the formula (1), as the group represented by Ar¹ and Ar², anunsubstituted or substituted arylene group and an unsubstituted orsubstituted divalent heterocyclic group are preferable.

In the formula (1), examples of the arylene group in Ar¹ and Ar² includea 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a1,4-naphthalenediyl group, a 2,6-naphthalenediyl group, a2,7-naphthalenediyl group, a 2,6-anthracenediyl group, a9,10-anthracenediyl group, a 2,7-phenanthrenediyl group, a5,12-naphthacenediyl group, 2,7-fluorenediyl, a 3,6-fluorenediyl group,a 1,6-pyrenediyl group, a 2,7-pyrenediyl group, or a 3,8-perylenediylgroup; the 1,4-phenylene group, 2,7-fluorenediyl, the 2,6-anthracenediylgroup, the 9,10-anthracenediyl group, the 2,7-phenanthrenediyl group,and the 1,6-pyrenediyl group are more preferable, and these may have asubstituent.

In the formula (1), examples of the divalent heterocyclic group in Ar¹and Ar² include a 2,5-pyrrolediyl group, a dibenzofurandiyl group, adibenzothiophenediyl group, a 2,1,3-benzothiadiazole-4,7-diyl group, a3,7-phenoxazinediyl group, or a 3,6-carbazolediyl group; these may havea substituent.

In the formula (1), examples of the divalent group in which two or moresame or different groups selected from arylene groups and divalentheterocyclic groups are linked in Ar¹ and Ar² include a grouprepresented by the following formula (1a-1), (1a-2), (1a-3), (1a-4),(1a-5), (1a-6), or (1a-7); these may have a substituent.

In the formula (1), “among R¹, R², R³, and R⁴, adjacent groups may belinked to each other to form a cyclic structure” means that among R¹,R², R³, and R⁴, groups bonded to the same carbon atom may be linked toeach other to form a cyclic structure, or when n¹ and/or n² is 2 ormore, groups bonded to carbon atoms in adjacent positions may be linkedto each other to form a cyclic structure.

In the formula (1), “among R⁷, R⁸, R⁹, and R¹⁰, adjacent groups may belinked to each other to form a cyclic structure” means that groupsbonded to carbon atoms in adjacent positions may be linked to each otherto form a cyclic structure, and for example, R⁸ and R⁹ may be linked toform a cyclic structure. Namely, the first constitutional unit can havea structure represented by, for example, the following formula (1b-1),(1b-2), (1b-3), (1b-4), (1b-5), or (1b-6):

The structure represented by the formula (1b-1) and the structurerepresented by the formula (1b-2) are examples in which R⁷ and R⁸ in theformula (1) are linked to each other to form a cyclic structure. Thestructure represented by the formula (1b-3), the structure representedby the formula (1b-4), and the structure represented by the formula(1b-5) are examples in which R⁸ and R⁹ in the formula (1) are linked toeach other to form a ring structure. The structure represented by theformula (1b-6) is an example in which R⁷, R⁸, R⁹, and R¹⁰ are linked toeach other to form a ring structure.

The formed cyclic structure may have a substituent; the substituent ispreferably an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, and a cyano group, more preferably analkyl group, an alkoxy group, an aryl group, an aryloxy group, anarylalkyl group, an arylalkoxy group, a substituted amino group, and anacyl group, cyano group, and still more preferably an alkyl group, analkoxy group, and an aryl group.

In the formula (1), because the luminance life of the light-emittingdevice using the polymer compound according to the present embodiment ismore excellent, it is preferable that n¹ and n² be an integer of 3 to 5,it is more preferable that n¹ and n² be an integer of 3 or 4, and it isstill more preferable that n¹ and n² be 3. n¹ and n² may be the same ordifferent from each other; it is preferable that n¹ and n² be the sameeach other because production of the monomer is easy.

In the formula (1), the expression “Ar¹ and R^(A) may be linked to eachother to form a ring structure, and Ar² and R^(B) may be linked to eachother to form a ring structure” means that the first constitutional unitcan have the structure represented by the following formula (1c-1),(1c-2), or (1c-3).

The formed ring structure may have a substituent; the substituent ispreferably an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, and a cyano group, more preferably analkyl group, an alkoxy group, an aryl group, an aryloxy group, anarylalkyl group, an arylalkoxy group, a substituted amino group, an acylgroup, and a cyano group, and still more preferably an alkyl group, analkoxy group, and an aryl group.

Examples of the first constitutional unit include constitutional unitsrepresented by the following formulas (1-1) to (1-21). Among theconstitutional units represented by the formulas (1-1) to (1-21), theconstitutional units represented by the formulas (1-1), (1-2), (1-3),(1-4), (1-6), (1-7), (1-8), (1-9), (1-11), (1-12), (1-13), (1-14), and(1-17) are preferable, the constitutional units represented by theformulas (1-1), (1-2), (1-3), (1-6), (1-7), (1-9), (1-11), and (1-14)are more preferable, and the constitutional units represented by theformulas (1-1), (1-2), (1-3), (1-6), (1-7), and (1-9) are still morepreferable because the luminance life of the light-emitting device to beobtained is more excellent in the case where the polymer compound isused in production of the light-emitting device.

As the first constitutional unit, the polymer compound may have only oneconstitutional unit above, or may have a plurality of differentconstitutional units among the constitutional units above.

(Second Constitutional Unit)

The second constitutional unit is a constitutional unit represented bythe following formula (2):

In the formula (2), Ar³ represents an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or different groupsselected from arylene groups and divalent heterocyclic groups are linked(the group may have a substituent). The constitutional unit representedby the formula (2) is different from the group represented by theformula (5) described later.

In the case where the group represented by Ar³ in the formula (2) has asubstituent, the substituent is preferably an alkyl group, an alkoxygroup, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, an arylalkenyl group, an arylalkynyl group, an aminogroup, a substituted amino group, a halogen atom, an acyl group, anacyloxy group, a monovalent heterocyclic group, a carboxyl group, anitro group, and a cyano group, more preferably an alkyl group, analkoxy group, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, an acyl group, a cyanogroup, and still more preferably an alkyl group, an alkoxy group, and anaryl group.

In the formula (2), as the group represented by Ar³, an unsubstituted orsubstituted arylene group, and an unsubstituted or substituted divalentheterocyclic group are preferable.

In the formula (2), examples of the arylene group in Ar³ include a1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a1,4-naphthalenediyl group, a 2,6-naphthalenediyl group, a2,7-naphthalenediyl group, a 2,6-anthracenediyl group, a9,10-anthracenediyl group, a 2,7-phenanthrenediyl group, a5,12-naphthacenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediylgroup, 1,6-pyrenediyl group, and a 3,8-perylenediyl group, and thearylene group may have the substituent above.

As Ar³ in the formula (2), a 1,3-phenylene group, a 1,4-phenylene group,a 2,6-naphthalenediyl group, a 2,7-naphthalenediyl group, a2,6-anthracenediyl group, a 9,10-anthracenediyl group, a2,7-phenanthrenediyl group, a 2,7-fluorenediyl group, and a3,6-fluorenediyl group are preferable because the luminance life of thelight-emitting device to be obtained is more excellent in the case wherethe polymer compound according to the present embodiment is used inproduction of the light-emitting device.

In the formula (2), examples of the divalent heterocyclic group in Ar³include a 2,5-pyrrolediyl group, a 2,1,3-benzothiadiazole-4,7-diylgroup, a dibenzofurandiyl group, and a dibenzothiophenediyl group, andthe divalent heterocyclic group may have the substituent above.

In the formula (2), as the divalent group in which two or more same ordifferent groups selected from arylene groups and divalent heterocyclicgroups are linked in Ar³, a group represented by the above formula(1a-1), (1a-2), (1a-3), (1a-4), (1a-5), (1a-6), or (1a-7) can beselected, and the divalent group may have the substituent above.

Examples of the second constitutional unit include the constitutionalunits represented by the following formulas (2-1) to (2-36). Among theconstitutional units represented by the formulas (2-1) to (2-36), theconstitutional units represented by the formulas (2-1), (2-2), (2-3),(2-4), (2-5), (2-6), (2-7), (2-8), (2-9), (2-10), (2-11), (2-12),(2-13), (2-14), (2-21), (2-22), (2-23), (2-25), (2-27), (2-28), (2-30),(2-32), (2-33), (2-35), and (2-36) are preferable, the constitutionalunits represented by the formulas (2-1), (2-2), (2-3), (2-4), (2-5),(2-6), (2-7), (2-8), (2-9), (2-10), (2-11), (2-12), (2-13), (2-14),(2-28), and (2-30) are more preferable, and the constitutional unitsrepresented by the formulas (2-1), (2-2), (2-4), (2-5), (2-12), (2-13),(2-14), and (2-30) are still more preferable because the luminance lifeof the light-emitting device to be obtained is more excellent in thecase where the polymer compound is used in production of thelight-emitting device.

As the second constitutional unit, the constitutional unit representedby the following formula (3) (constitutional unit including the grouprepresented by the following formula (3′)) is also preferable:

In the formula (3) and the formula (3′), a¹ and a² each independentlyrepresent an integer of 0 to 4; a³ represents an integer of 0 to 5. R¹¹,R¹², and R¹³ each independently represent an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted alkoxy group,an unsubstituted or substituted aryl group, an unsubstituted orsubstituted aryloxy group, an unsubstituted or substituted monovalentheterocyclic group, an unsubstituted or substituted alkoxycarbonylgroup, an unsubstituted or substituted silyl group, a halogen atom, aR¹³, carboxyl group, or a cyano group. When R¹¹, R¹², R¹³, and R¹⁴ existin plural, the plurality of R¹¹, R¹², R¹³, or R¹⁴ may be the same ordifferent from each other.

In the formula (3) and the formula (3′), it is preferable that a¹ and a²be an integer of 0 to 2, and a³ be an integer of 1 to 3 because theluminance life of the light-emitting device using the polymer compoundaccording to the present embodiment is more excellent.

In the formula (3) and the formula (3′), in the case where the grouprepresented by R¹¹, R¹², and R¹³ has a substituent, the substituent ispreferably an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, and a cyano group, more preferably analkyl group, an alkoxy group, an aryl group, an aryloxy group, anarylalkyl group, an arylalkoxy group, a substituted amino group, an acylgroup, a cyano group, and still more preferably an alkyl group, analkoxy group, and an aryl group.

In the formula (3) and the formula (3′), examples of R¹¹, R¹², and R¹³include an unsubstituted or substituted alkyl group, an unsubstituted orsubstituted alkoxy group, and an unsubstituted or substituted arylgroup. Here, examples of the substituted alkyl group in R¹¹, R¹², andR¹³ include an arylalkyl group or an alkylarylalkyl group. Examples ofthe substituted alkoxy group in R¹¹, R¹², and R¹³ include an arylalkoxygroup and an alkoxy group substituted with an alkoxy group. Examples ofthe substituted aryl group in R¹¹, R¹², and R¹³ include an alkyl arylgroup.

It is preferable that R¹¹, R¹², and R¹³ be an unsubstituted orsubstituted alkyl group, or an unsubstituted or substituted aryl groupbecause the luminance life of the light-emitting device using thepolymer compound according to the present embodiment is more excellent.

It is preferable that as the second constitutional unit, the polymercompound have a constitutional unit consisting of an unsubstituted orsubstituted fluorenediyl group, and it is more preferable that as thethird constitutional unit, the polymer compound have a constitutionalunit consisting of an unsubstituted or substituted 2,7-fluorenediylgroup.

It is preferable that as the second constitutional unit, the polymercompound have a constitutional unit consisting of at least one groupselected from the group consisting of an unsubstituted or substitutedphenylene group, an unsubstituted or substituted naphthalenediyl group,an unsubstituted or substituted anthracenediyl group, and the grouprepresented by the above formula (3′).

It is preferable that the content (total content) of the secondconstitutional unit be 0.1 to 99.9 mol % of the total constitutionalunits, it is more preferable that the content (total content) of thethird constitutional unit be 30 to 99.9 mol % of the totalconstitutional units, and it is still more preferable that the content(total content) of the third constitutional unit be 50 to 99.9 mol % ofthe total constitutional units because the luminance life of thelight-emitting device to be obtained is more excellent in the case wherethe polymer compound is used in production of the light-emitting device.

As the second constitutional unit, the polymer compound may have onlyone constitutional unit above, or may have a plurality of differentconstitutional units among the constitutional units above. The polymercompound may have the first constitutional unit, the thirdconstitutional unit described later, the constitutional unit includingan unsubstituted or substituted fluorenediyl group, and theconstitutional unit including an unsubstituted or substituted phenylenegroup.

The polymer compound may have the first constitutional unit, the thirdconstitutional unit, the constitutional unit including an unsubstitutedor substituted fluorenediyl group, and the constitutional unit includingan unsubstituted or substituted naphthalenediyl group.

The polymer compound may have the first constitutional unit, the thirdconstitutional unit, the constitutional unit including an unsubstitutedor substituted fluorenediyl group, and the constitutional unit includingan unsubstituted or substituted anthracenediyl group.

The polymer compound may have the first constitutional unit, the thirdconstitutional unit, the constitutional unit including an unsubstitutedor substituted fluorenediyl group, and the constitutional unitrepresented by the above formula (3).

(Third Constitutional Unit)

The third constitutional unit is a constitutional unit represented bythe following formula (4):

wherein b¹ and b² each independently represent 0 or 1; Ar⁴, Ar⁵, Ar⁶,and Ar⁷ each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or different groupsselected from arylene groups and divalent heterocyclic groups are linked(the group may have a substituent); R^(C), R^(D), and R^(E) eachindependently represent a hydrogen atom, an unsubstituted or substitutedalkyl group, an unsubstituted or substituted aryl group, or anunsubstituted or substituted monovalent heterocyclic group; Ar⁴, Ar⁵,Ar⁶, and Ar⁷ may be linked to each other to form a ring structure.

In the formula (4), it is more preferable that b¹ be 1 because theluminance life of the light-emitting device using the polymer compoundaccording to the present embodiment is more excellent.

In the formula (4), it is preferable that b² be 0 because synthesis ofthe monomer is easy and the light emission efficiency of thelight-emitting device using the polymer compound according to thepresent embodiment is more excellent.

In the formula (4), it is preferable that R^(C), R^(D), and R^(E) be asubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group, and it ismore preferable that R^(C), R^(D), and R^(E) be an unsubstituted orsubstituted aryl group because the stability of the polymer compoundaccording to the present embodiment is good and the luminance life ofthe light-emitting device using the polymer compound is more excellent.

In the case where the groups represented by Ar⁴, Ar⁵, Ar⁶, and Ar⁷ havea substituent in the formula (4), examples of the substituent include analkyl group, an alkoxy group, an aryl group, an aryloxy group, anarylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, and a cyano group; the substituent ispreferably an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, a substituted aminogroup, acyl group, and a cyano group, and more preferably an alkylgroup, an alkoxy group, and an aryl group.

In the formula (4), it is preferable that the groups represented by Ar⁴,Ar⁵, Ar⁶, and Ar⁷ be an unsubstituted or substituted arylene group or anunsubstituted or substituted divalent heterocyclic group, andparticularly an unsubstituted or substituted arylene group because thestability of the polymer compound according to the present embodiment isgood and the luminance life of the light-emitting device using thepolymer compound is more excellent.

In the formula (4), examples of the arylene group in Ar⁴, Ar⁵, Ar⁶, andAr⁷ include a 1,2-phenylene group, a 1,3-phenylene group, a1,4-phenylene group, a 1,4-naphthalenediyl group, a 2,6-naphthalenediylgroup, a 2,7-naphthalenediyl group, a 2,6-anthracenediyl group, a9,10-anthracenediyl group, a 2,7-phenanthrenediyl group, a5,12-naphthacenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediylgroup, a 1,6-pyrenediyl group, a 2,7-pyrenediyl group, or a3,8-perylenediyl group; the 1,4-phenylene group, the 2,7-fluorenediylgroup, the 2,6-anthracenediyl group, the 9,10-anthracenediyl group, the2,7-phenanthrenediyl group, and the 1,6-pyrenediyl group are preferable;these may have a substituent.

In the formula (4), examples of the divalent heterocyclic group in theAr⁴, Ar⁵, Ar⁶, and Ar⁷ include a 2,5-pyrrolediyl group, adibenzofurandiyl group, a dibenzothiophenediyl group, and a2,1,3-benzothiadiazole-4,7-diyl group; these may have a substituent. Thedivalent heterocyclic group represented by Ar⁴, Ar⁵, Ar⁶, and Ar⁷ isdifferent from the group represented by the formula (5).

In the formula (4), examples of the divalent group in which two or moresame or different groups selected from arylene groups and divalentheterocyclic groups are linked in Ar⁴, Ar⁵, Ar⁶, and Ar⁷ include a grouprepresented by the above formula (1a-1), (1a-2), (1a-3), (1a-4), (1a-5),(1a-6), or (1a-7); the group represented by the above formula (1a-1) ispreferable; these may have a substituent.

In the case where the groups represented by R^(C), R^(D), and R^(E) havea substituent in the formula (4), the substituent is preferably an alkylgroup, an alkoxy group, an aryl group, an aryloxy group, an arylalkylgroup, an arylalkoxy group, an arylalkenyl group, an arylalkynyl group,an amino group, a substituted amino group, a halogen atom, an acylgroup, an acyloxy group, a monovalent heterocyclic group, a carboxylgroup, a nitro group, and a cyano group, more preferably an alkyl group,an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, acyl group, and a cyanogroup, and still more preferably an alkyl group, an alkoxy group, and anaryl group.

In the formula (4), the alkyl group in R^(C), R^(D), and R^(E) is thesame “alkyl group” described as the term commonly used; the alkyl groupis preferably a C₁ to C₂₀ alkyl group; these may have a substituent.

In the formula (4), the aryl group in R^(C), R^(D), and R^(E) is thesame “aryl group” described as the term commonly used; the aryl group ispreferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, and a2-fluorenyl group; these may have a substituent.

In the formula (4), the monovalent heterocyclic group in R^(C), R^(D),and R^(E) is the same “monovalent heterocyclic group” described as theterm commonly used; the monovalent heterocyclic group is preferably apyridyl group, a pyrimidyl group, a triazyl group, and a quinolyl group;these may have a substituent.

Examples of the third constitutional unit include the constitutionalunits represented by the following formulas (3-a), (3-b), (3-c), and(3-d); because the luminance life of the light-emitting device using thepolymer compound according to the present embodiment is more excellent,the constitutional units represented by the formulas (3-b), (3-c), and(3-d) are preferable, and the constitutional unit represented by theformula (3-c) is more preferable.

wherein R⁵² represents a hydrogen atom, an alkyl group, an alkoxy group,an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxygroup, an arylalkenyl group, an arylalkynyl group, an amino group, asubstituted amino group, a halogen atom, an acyl group, an acyloxygroup, a monovalent heterocyclic group, a carboxyl group, a nitro group,or a cyano group. R⁵² is preferably an alkyl group, an alkoxy group, anaryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, asubstituted amino group, an acyl group, or a cyano group, and morepreferably an alkyl group, an alkoxy group, or an aryl group. Aplurality of R⁵² present may be the same or different from each other.R⁵² may form a ring with other R⁵² instead of representing the group.

The third constitutional unit may be a constitutional unit representedby the following formula (2A):

wherein s and t each independently represent an integer of 0 to 4; u is1 or 2; v is an integer of 0 to 5; R⁵³, R⁵⁴, and R⁵⁵ each independentlyrepresent an alkyl group, an alkoxy group, an aryl group, an aryloxygroup, an arylalkyl group, an arylalkoxy group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a halogenatom, an acyl group, an acyloxy group, a monovalent heterocyclic group,a carboxyl group, a nitro group, or a cyano group; when R⁵³, R⁵⁴, andR⁵⁵ exist in plural, the plurality of R⁵³, R⁵⁴, or R⁵⁵ may be the sameor different from each other; among the plurality of R⁵³ present,adjacent groups may be linked to each other to form a ring structure;and among the plurality of R⁵⁴ present, adjacent groups may be linked toeach other to form a ring structure.

In the formula (2A), it is preferable that s and t each independentlyrepresent 0 to 2, u be 2, and v be 1 to 5 because the luminance life ofthe light-emitting device using the polymer compound according to thepresent embodiment is more excellent. v is more preferably 1 to 3.

In the formula (2A), it is preferable that R⁵³, R⁵⁴, and R⁵⁵ be an alkylgroup, an alkoxy group, or an aryl group because the luminance life ofthe light-emitting device using the polymer compound according to thepresent embodiment is more excellent.

The third constitutional unit may be a constitutional unit representedby the following formula (5):

wherein R^(F) represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; X¹represents a single bond, an oxygen atom, a sulfur atom, or a grouprepresented by —C(R¹⁴)₂—; R¹⁴ represents an unsubstituted or substitutedalkyl group or an unsubstituted or substituted aryl group. A pluralityof R¹⁴ may be the same or different from each other.

It is preferable that R^(F) be an unsubstituted or substituted alkylgroup, an unsubstituted or substituted aryl group, or an unsubstitutedor substituted monovalent heterocyclic group, it is more preferable thatR^(F) be an unsubstituted or substituted alkyl group or an unsubstitutedor substituted aryl group, and it is still more preferable that R^(F) bean unsubstituted or substituted aryl group because the stability of thepolymer compound according to the present embodiment is good and theluminance life of the light-emitting device using the polymer compoundis more excellent.

In the formula (5), it is preferable that X¹ be a single bond or anoxygen atom, and it is more preferable that X¹ be an oxygen atom becausewhen the polymer compound is used in production of the light-emittingdevice, the luminance life of the light-emitting device to be obtainedis more excellent.

In the case where the group represented by R^(F) in the formula (5) hasa substituent, the substituent is preferably an alkyl group, an alkoxygroup, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, an arylalkenyl group, an arylalkynyl group, an aminogroup, a substituted amino group, a halogen atom, an acyl group, anacyloxy group, a monovalent heterocyclic group, a carboxyl group, anitro group, or a cyano group, more preferably an alkyl group, an alkoxygroup, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, an acyl group, or a cyanogroup, and still more preferably an alkyl group, an alkoxy group, or anaryl group.

In the formula (5), the alkyl group in R^(F) is the same “alkyl group”described as the term commonly used; the alkyl group is preferably a C₁to C₂₀ alkyl group; these may have a substituent.

In the formula (5), the aryl group in R^(F) is the same “aryl group”described as the term commonly used; the aryl group is preferably aphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenylgroup, a 2-anthracenyl group, a 9-anthracenyl group, and a 2-fluorenylgroup; these may have a substituent.

In the formula (5), the monovalent heterocyclic group in R^(F) is thesame “monovalent heterocyclic group” described as the term commonlyused; the monovalent heterocyclic group is preferably a pyridyl group, apyrimidyl group, a triazyl group, and a quinolyl group; these may have asubstituent.

In the case where the group represented by R¹⁴ in the formula (5) has asubstituent, the substituent is preferably an alkyl group, an alkoxygroup, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, an arylalkenyl group, an arylalkynyl group, an aminogroup, a substituted amino group, a halogen atom, an acyl group, anacyloxy group, a monovalent heterocyclic group, a carboxyl group, anitro group, or a cyano group, more preferably an alkyl group, an alkoxygroup, an aryl group, an aryloxy group, an arylalkyl group, anarylalkoxy group, a substituted amino group, an acyl group, or a cyanogroup, and still more preferably an alkyl group, an alkoxy group, or anaryl group.

In the formula (5), the alkyl group in R¹⁴ is the same “alkyl group”described as the term commonly used; the alkyl group is preferably a C₁to C₂₀ alkyl group; these may have a substituent.

In the formula (5), the aryl group in R¹⁴ is the same “aryl group”described as the term commonly used; the aryl group is preferably aphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenylgroup, a 2-anthracenyl group, a 9-anthracenyl group, and a 2-fluorenylgroup; these may have a substituent.

Examples of the third constitutional unit include the constitutionalunits represented by the following formulas (3-1) to (3-12). Among theconstitutional units represented by the following formulas (3-1) to(3-12), the constitutional units represented by the formulas (3-1),(3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), and(3-12) are preferable, the constitutional units represented by theformulas (3-1), (3-2), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), and(3-10) are more preferable, and the constitutional units represented bythe formulas (3-2), (3-4), (3-8), and (3-9) are still more preferablebecause the luminance life of the light-emitting device to be obtainedis more excellent in the case where the polymer compound is used inproduction of the light-emitting device.

It is preferable that the content of the third constitutional unit be0.1 to 70 mol % of all the constitutional units, it is more preferablethat the content of the third constitutional unit be 0.1 to 50 mol % ofall the constitutional units, and it is still more preferable that thecontent of the third constitutional unit be 0.1 to 40 mol % of all theconstitutional units because the luminance life of the light-emittingdevice to be obtained is more excellent in the case where the polymercompound is used in production of the light-emitting device.

As the third constitutional unit, the polymer compound may have only oneconstitutional unit, or may have a plurality of different constitutionalunits among the constitutional units above.

Examples of a combination of the constitutional units in the polymercompound are shown below:

The polymer compound is synthesized by condensation polymerization of amonomer (1) that introduces the constitutional unit represented by theformula (1) with a monomer (X) that introduces a constitutional unitdifferent from the constitutional unit, and when the number of themonomer (1) is N₁ and the number of the monomer (X) is N_(X), it ispreferable that N₁ and N_(X) satisfy the following formula (I), and itis more preferable that N₁ and N_(X) satisfy the following formula (II):0.1≦N ₁×100/(N ₁ +N _(X))≦50  (I)0.1≦N ₁×100/(N ₁ +N _(X))≦40  (II)

Examples of the monomer (1) include the compound represented by theformula (1M) described later. Examples of the monomer (X) include thecompound represented by the formula (2M) and the compound represented bythe formula (4M) described later.

If a polymerizable group remains as it is in the terminal group, thepolymer compound according to the present embodiment has a possibilityof reducing the light emission properties and life of the light-emittingdevice produced using the polymer compound. For this reason, it ispreferable that the terminal group be a stable group (such as an arylgroup and a monovalent heterocyclic group (particularly, a monovalentaromatic heterocyclic group)).

The polymer compound according to the present embodiment, when it is acopolymer, may be any copolymer; for example, the polymer compoundaccording to the present embodiment may be any of block copolymers,random copolymers, alternating copolymers, and graft copolymers.

The polymer compound according to the present embodiment is useful aslight-emitting materials, charge transport materials, and the like, andmay be used in combination with other compound as a compositiondescribed later.

The polystyrene-equivalent number-average molecular weight (Mn) of thepolymer compound according to the present embodiment measured by gelpermeation chromatography (hereinafter, referred to as “GPC”) is usually1×10³ to 1×10⁸, and preferably 1×10⁴ to 5×10⁶. Thepolystyrene-equivalent weight-average molecular weight (Mw) of thepolymer compound according to the present embodiment is usually 1×10³ to1×10⁸, and preferably 1×10⁴ to 1×10⁷ because film forming properties aregood and the luminance life of the light-emitting device to be obtainedusing the polymer compound is more excellent.

It is preferable that the glass transition temperature of the polymercompound according to the present embodiment be 70° C. or more becausedurability against various processes for producing the light-emittingdevice is high and the heat resistance of the light-emitting device isgood.

The light-emitting device using the polymer compound is a highperformance light-emitting device that can be derived with excellentluminance life. Accordingly, the light-emitting device is useful forbacklights of liquid crystal displays, curved or flat light sources forlighting, segment display devices, dot matrix display devices, and thelike. Further, the polymer compound according to the present embodimentcan also be used as a dye for a laser, a material for an organic solarcell, an organic semiconductor for an organic transistor, a material fora conductive film such as conductive films and organic semiconductorfilms, and a light-emittable film material that emits fluorescence orphosphorescence.

(Method for Producing Polymer Compound)

In the case where the polymer compound is a copolymer, the polymercompound can be produced, for example, by condensation polymerizing thecompound represented by the following formula (1M) (hereinafter,referred to as a “compound 1M” depending on cases) with other monomer(such as the compound represented by the following formula (2M)(hereinafter, referred to as a “compound 2M” depending on cases) and/orthe compound represented by the following formula (4M) (hereinafter,referred to as a “compound 4M” depending on cases)).

In the case where the polymer compound is a homopolymer, the polymercompound can be produced, for example, by condensation polymerizing thecompound 1M.

Herein, the compound 1M, the compound 2M, and a compound 4M arecollectively referred to as the “monomer” in some cases.

In the formula (1M), n¹, n², R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰,Ar¹, Ar², R^(A), and R^(B) are the same as above; Z¹ and Z² eachindependently represent a group selected from the following substituentgroups (the following substituent group A or the following substituentgroup B).

In the formula (2M), Ar³ is the same as above; Z³ and Z⁴ represent agroup selected from the following substituent group A or the followingsubstituent group B.

In the formula (4M), b¹, b², Ar⁴, Ar⁵, Ar⁶, Ar⁷, R^(C), R^(D), and R^(E)are the same as above; Z⁵ and Z⁶ represent a group selected from thefollowing substituent group A or the substituent group B.

<Substituent Group A>

Groups represented by a chlorine atom, a bromine atom, an iodine atom,and —O—S(═O)₂R⁴¹ (R⁴¹ represents an alkyl group, or an aryl group whichmay be substituted by alkyl group, alkoxy group, nitro group, fluorineatom, or a cyano group).

<Substituent Group B>

Groups represented by —B(OR⁴²)₂ (R⁴² represents a hydrogen atom or analkyl group; and a plurality of R⁴² present may be the same or differentfrom each other and may be linked to each other to form a cyclicstructure); groups represented by —BF₄Q¹ (Q¹ represents a monovalentcation selected from the group consisting of Li⁺, Na⁺, K⁺, Rb⁺, andCs⁺); groups represented by —MgY¹ (Y¹ represents a chlorine atom, abromine atom, or an iodine atom); groups represented by —ZnY² (Y²represents a chlorine atom, a bromine atom, or an iodine atom); andgroups represented by —Sn(R⁴³)₃ (R⁴³ represents a hydrogen atom or analkyl group; and a plurality of R⁴³ present may be the same or differentfrom each other and may be linked to each other to form a cyclicstructure).

It is known that the compound having the group selected from thesubstituent group A and the compound having the group selected from thesubstituent group B are condensation polymerized by a known couplingreaction, and carbon atoms bonded to the groups are bonded. For thisreason, if the compound A having two groups selected from thesubstituent group A and the compound B having two groups selected fromthe substituent group B are fed to the known coupling reaction, acondensation polymer of the compound A and the compound B can beobtained by condensation polymerization.

For example, in the case where Z¹ and Z² in the compound 1M are a groupselected from the substituent group A, a group selected from thesubstituent group B can be selected as Z³ and Z⁴ (or Z⁵ and Z⁶) in thecompound 2M (or the compound 4M). In the case where Z¹ and Z² in thecompound 1M are a group selected from the substituent group B, a groupselected from the substituent group A can be selected as Z³ and Z⁴ (orZ⁵ and Z⁶) in the compound 2M (or the compound 4M).

A condensation polymer can also be obtained, for example, by a methodfor polymerizing the compound having two groups selected from thesubstituent group A with an Ni(0) catalyst (Yamamoto polymerization)(Progress in Polymer Science, Vol. 17, pp. 1153 to 1205, 1992).

In such condensation polymerization, the first constitutional unit isintroduced by the compound 1M, the second constitutional unit isintroduced by the compound 2M, and the third constitutional unit isintroduced by the compound 4M.

Examples of the condensation polymerization method include a method forpolymerization using the Suzuki coupling reaction (Chem. Rev.), Vol. 95,pp. 2457-2483 (1995)), a method for polymerization using the Grignardreaction (Bull. Chem. Soc. Jpn., Vol. 51, p. 2091 (1978)), a method forpolymerization using an Ni(0) catalyst (Progress in Polymer Science,Vol. 17, pp. 1153 to 1205, 1992), and a method using the Stille couplingreaction (European Polymer Journal), Vol. 41, pp. 2923-2933 (2005)).Among these, from the viewpoint of easy synthesis of raw materials andsimple operation of the polymerization reaction, the method forpolymerization using the Suzuki coupling reaction and the method forpolymerization using an Ni(0) catalyst are preferable; considering easycontrol of the structure of the polymer compound, a method forpolymerization using an aryl-aryl cross coupling reaction such as theSuzuki coupling reaction, the Grignard reaction, and the Stille couplingreaction is more preferable; the reaction using the polymerization bythe Suzuki coupling reaction is particularly preferable.

Examples of the condensation polymerization method include a method ofreacting the compounds above with a proper catalyst or base whennecessary. In the case where the method for polymerization using theSuzuki coupling reaction is selected, in order to obtain the polymercompound having a desired molecular weight, the ratio of the total molenumber of the group selected from substituent group B that each compoundhas to the total mole number of the group selected from the substituentgroup A that each compound has may be adjusted. Usually, it ispreferable that the ratio of the latter mole number to the former molenumber be 0.95 to 1.05, it is more preferable that the ratio of thelatter mole number to the former mole number be 0.98 to 1.02, and it isstill more preferable that the ratio of the latter mole number to theformer mole number be 0.99 to 1.01.

It is preferable that the amount of the compound 1M to be used in thecondensation polymerization be 0.1 to 70 mol % based on the total molaramount of the compound 1M and other monomer, it is more preferable thatthe amount of the compound 1M to be used in the condensationpolymerization be 0.1 to 50 mol % based on the total molar amount of thecompound 1M and other monomer, and it is still more preferable that theamount of the compound 1M to be used in the condensation polymerizationbe 0.1 to 40 mol % based on the total molar amount of the compound 1Mand other monomer. In the case where the compound 2M is used in thecondensation polymerization, it is preferable that the amount of thecompound 2M to be used be 0.1 to 99.9 mol % based on the total molaramount of the compound 2M and the other monomer, it is more preferablethat the amount of the compound 2M to be used be 30 to 99.9 mol % basedon the total molar amount of the compound 2M and the other monomer, andit is still more preferable that the amount of the compound 2M to beused be 50 to 99.9 mol % based on the total molar amount of the compound2M and the other monomer. In the case where the compound 4M is used inthe condensation polymerization, it is preferable that the amount of thecompound 4M be 0.1 to 70 mol % based on the total molar amount of thecompound 4M and the other monomer, it is more preferable that the amountof the compound 4M be 0.1 to 50 mol % based on the total molar amount ofthe compound 4M and the other monomer, and it is still more preferablethat the amount of the compound 4M be 0.1 to 40 mol % based on the totalmolar amount of the compound 4M and the other monomer. According to suchcondensation polymerization, a polymer compound that satisfies the aboveformula (I) can be obtained.

The monomer synthesized in advance and separated may be used, or themonomer may be synthesized during the reaction system and used as it is.In the case where the polymer compound to be obtained is used for thelight-emitting device, the purity may affect the performance of thelight-emitting device. For this reason, it is preferable that thesemonomers be refined by a method such as distillation, chromatography,sublimation refining, recrystallization or a combination thereof.

In the method of producing the polymer compound according to the presentembodiment, it is preferable that the monomers be polymerized in thepresence of a catalyst. In the case where polymerization is performedusing the Suzuki coupling reaction, examples of the catalyst includetransition metal complexes such as palladium complexes such aspalladium[tetrakis(triphenylphosphine)],[tris(dibenzylideneacetone)]dipalladium, palladium acetate, anddichlorobistriphenylphosphinepalladium; and complexes in which a ligandsuch as triphenylphosphine, tri-tert-butylphosphine, andtricyclohexylphosphine is coordinated with these transition metalcomplexes.

In the case where the polymerization is performed using the Ni(0)catalyst, examples of the Ni(0) catalyst include transition metalcomplexes such as nickel complexes such asnickel[tetrakis(triphenylphosphine)],[1,3-bis(diphenylphosphino)propane]dichloronickel,[bis(1,4-cyclooctadiene)]nickel; and complexes in which a ligand such astriphenylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine,diphenylphosphinopropane, a substituted or unsubstituted bupyridyl, anda substituted or unsubstituted phenanthroline is coordinated with thesetransition metal complexes.

The catalyst synthesized in advance may be used, or the catalystprepared during the reaction system may be used as it is. Thesecatalysts may be used alone or in combination.

The amount of the catalyst may be an effective amount as the catalyst;for example, the amount in terms of the mole number of the transitionmetal is usually 0.0001 to 300 mol %, preferably 0.001 to 50 mol %, andmore preferably 0.01 to 20 mol % based on 100 mol % of the total of allthe monomers in the polymerization reaction.

In the method for polymerization using the Suzuki coupling reaction, itis preferable that a base be used. Examples of the base includeinorganic salt groups such as sodium carbonate, potassium carbonate,cesium carbonate, potassium fluoride, cesium fluoride, and tripotassiumphosphate; and organic bases such as tetrabutylammonium fluoride,tetrabutylammonium chloride, tetrabutylammonium bromide,tetraethylammonium hydroxide, and tetrabutylammonium hydroxide.

The amount of the base is usually 50 to 2000 mol %, and preferably 100to 1000 mol % based on 100 mol % of the total of all the monomers in thepolymerization reaction.

The polymerization reaction may be performed in the absence of asolvent, or performed in the presence of a solvent; usually, thepolymerization reaction is performed in the presence of an organicsolvent. Here, examples of the organic solvent include toluene, xylene,mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane,N,N-dimethylacetoamide, and N,N-dimethylformamide. Usually, in order tosuppress a side reaction, it is desired that a solvent subjected to adeoxidation treatment be used. The organic solvents may be used alone orin combination.

It is preferable that the amount of the organic solvent to be used be anamount such that the total concentration of all the monomers in thepolymerization reaction is 0.1 to 90% by weight, it is more preferablethat the amount of the organic solvent to be used be an amount such thatthe total concentration of all the monomers in the polymerizationreaction is 1 to 50% by weight, and it is still more preferable that theamount of the organic solvent to be used be an amount such that thetotal concentration of all the monomers in the polymerization reactionis 2 to 30% by weight.

The reaction temperature of the polymerization reaction is preferably−100 to 200° C., more preferably −80 to 150° C., and still morepreferably 0 to 120° C. The reaction time is usually 1 hour or more, andpreferably 2 to 500 hours.

In the polymerization reaction, to avoid remaining of the polymerizablegroup (such as Z¹, Z²) at the terminal in the polymer compound accordingto the present embodiment, a compound represented by the followingformula (1T) may be used as a chain-terminating agent. Thereby, apolymer compound whose terminal is the aryl group or monovalentheterocyclic group (particularly, the monovalent aromatic heterocyclicgroup) can be obtained.Z^(T)—Ar^(T)  (1T)

wherein Ar^(T) represents an aryl group that may have a substituent or amonovalent heterocyclic group (particularly, a monovalent aromaticheterocyclic group) that may have a substituent; Z^(T) represents thegroup selected from the substituent group A and the substituent group Babove. Examples of the aryl group and the monovalent heterocyclic group(particularly, the monovalent aromatic heterocyclic group) in Ar^(T) caninclude the aryl groups and monovalent heterocyclic groups(particularly, the monovalent aromatic heterocyclic groups) exemplifiedas R¹ above.

A post-treatment in the polymerization reaction can be performed by aknown method; for example, a method of removing water-soluble impuritiesby separation of a solution, a method in which a precipitate obtained byadding the reaction solution after the polymerization reaction to alower alcohol such as methanol is filtered and dried, and the like canbe used alone or in combination.

In the case where the purity of the polymer compound according to thepresent embodiment is low, refining may be performed by the standardmethod such as recrystallization, reprecipitation, continuous extractionwith a Soxhlet extractor, and column chromatography; in the case wherethe polymer compound according to the present embodiment is used for thelight-emitting device, the purity may affect the performance of thelight-emitting device such as light emission properties; for thisreason, it is preferable that after the condensation polymerization, apurifying treatment such as reprecipitation refining and separation bychromatography be performed.

(Compound)

The compound according to the present embodiment is a compoundrepresented by the following formula (1M):

wherein n¹, n², R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, Ar¹, Ar², R^(A),and R^(B) are the same as above; Z¹ and Z² each independently representa group selected from the substituent group (the substituent group A orsubstituent group B above).

For example, in the case where n¹ and/or n² is 2 or more in the formula(1M) and has a substituent, R¹ and R² are different from each other, andR³ and R⁴ are different from each other, a stereoisomer(diastereoisomer/enantiomer) can exist in the compound according to thepresent embodiment. The compound according to the present embodiment maybe composed of only a single stereoisomer, or may be a mixture ofdifferent stereoisomers.

Hereinafter, a method of producing the compound represented by theformula (1M) will be described using an example in which n¹ and n² are3. The compound represented by the formula (1M) can be produced by themethods according to the following Schemes 1 to 5.

wherein the wavy line indicates that the compound having the wavy lineis a geometric isomer mixture.

In Scheme 1, Y^(1a) and Y^(2a) each independently represent a hydrogenatom or a group selected from the substituent group A; Z^(1a) and Z^(2a)represent a hydrogen atom or a group selected from the substituent groupA; R^(1a) represents an unsubstituted or substituted alkyl group, anunsubstituted or substituted aryl group, or an unsubstituted orsubstituted monovalent heterocyclic group; Ar¹, Ar², R^(A), and R^(B)are the same as above; and a plurality of R^(1a) present may be the sameor different from each other.

In Scheme 1, first, by feeding the compound represented by the formula(6-1-1) (hereinafter, referred to as a “compound (6-1-1).” Hereinafter,the same is true of the compound represented by the formula (6-1-2)) tothe Wittig reaction, the Horner-Wadsworth-Emmons reaction, or the like,a compound (6-1-2) is obtained. Next, by feeding the compound (6-1-2) tothe reduction reaction, a compound (6-1-3) is obtained.

Here, in the case where Y^(1a) and Y^(2a) are a hydrogen atom, thecompound (6-1-3) is fed to a reaction such as a bromination reaction,and Y^(1a) and Y^(2a) are converted into the group selected from thesubstituent group A.

Next, by a coupling reaction of the compound (6-1-3) with apredetermined amine compound, the compound (6-1-5) is obtained via thecompound (6-1-4). In the case where the Z^(1a) and Z^(1b) in thecompound (6-1-5) are a hydrogen atom, by feeding the compound (6-1-5) toa reaction such as a bromination reaction, the hydrogen atom can beconverted to the group selected from the substituent group A. In thecase where the Z^(1a) and Z^(1b) in the compound (6-1-5) are the groupselected from the substituent group A, the group can be converted to thegroup selected from the substituent group B by a known reaction.

In Scheme 2, aa represents 0 or 1; Y^(1b) and Y^(2b) each independentlyrepresent a hydrogen atom or the group selected from the substituentgroup A; Z^(1b) and Z^(2b) each independently represent a hydrogen atomor the group selected from the substituent group A; Z^(A) represents thegroup selected from the substituent group A; R^(1b) represents anunsubstituted or substituted alkyl group, an unsubstituted orsubstituted aryl group, or an unsubstituted or substituted monovalentheterocyclic group. Ar¹, Ar², R^(A), and R^(B) are the same as above. Aplurality of aa present may be the same or different from each other. Inthe case where a plurality of R^(1b) are present, those may be the sameor different.

In Scheme 2, first, in the presence of a base, a compound (6-2-2) isobtained by an addition reaction of the compound (6-2-1) andR^(1b)—Z^(A). Next, by feeding the compound (6-2-2) to the reductionreaction, a compound (6-2-3) is obtained.

Here, in the case where Y^(1b) and Y^(2b) are a hydrogen atom, thecompound (6-2-3) is fed to a reaction such as a bromination reaction,and Y^(1b) and Y^(2b) are converted into the group selected from thesubstituent group A.

Next, by a coupling reaction of the compound (6-2-3) with apredetermined amine compound, the compound (6-2-5) is obtained via thecompound (6-2-4). In the case where Z^(1b) and Z^(2b) in the compound(6-2-5) are a hydrogen atom, by feeding the compound (6-2-5) to thereaction such as the bromination reaction, the hydrogen atom can beconverted to the group selected from the substituent group A. In thecase where Z^(1b) and Z^(2b) in the compound (6-2-5) are the groupselected from the substituent group A, the group can be converted to thegroup selected from the substituent group B by a known reaction.

In Scheme 3, Y^(1c) and Y^(2c) each independently represent a hydrogenatom or a group selected from the substituent group A; Z^(1c) and Z^(2c)each independently represent a hydrogen atom or a group selected fromthe substituent group A; R^(1c) represents an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; M¹represents an alkali metal such as lithium and potassium or a grouprepresented by -M^(II)Z^(H), Ar¹, Ar², R^(A), and R^(B) are the same asabove; M^(II) represents Mg or Zn; Z^(H) represents a halogen atom; anda plurality of R^(1c) present may be the same or different from eachother.

In Scheme 3, first, a compound (6-3-2) is obtained by a reaction of thecompound (6-3-1) with R^(1c)-M¹. Next, a compound (6-3-3) is obtained byconverting a hydroxyl group to a hydrogen atom in the compound (6-3-2)by a known reaction.

Here, in the case where Y^(1c) and Y^(2c) are a hydrogen atom, thecompound (6-3-3) is fed to a reaction such as a bromination reaction,and Y^(1c) and Y^(2c) are converted into the group selected from thesubstituent group A.

Next, by a coupling reaction of the compound (6-3-3) with apredetermined amine compound, the compound (6-3-5) is obtained via thecompound (6-3-4). In the case where Z^(1c) and Z^(2c) in the compound(6-3-5) are a hydrogen atom, by feeding the compound (6-3-5) to thereaction such as the bromination reaction, the hydrogen atom can beconverted to the group selected from the substituent group A. In thecase where Z^(1c) and Z^(2c) in the compound (6-3-5) are the groupselected from the substituent group A, the group can be converted to thegroup selected from the substituent group B by a known reaction.

In Scheme 4, Y^(1d) and Y^(2d) each independently represent a hydrogenatom or a group selected from the substituent group A; Z^(1d) and Z^(2d)each independently represent a hydrogen atom or a group selected fromthe substituent group A; R^(1d) represents an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; M²represents an alkali metal such as lithium and potassium or a grouprepresented by -M^(II)Z^(H); M^(II) represents Mg or Zn; Z^(H)represents a halogen atom.

In Scheme 4, first, a compound (6-4-2) is obtained by a reaction of thecompound (6-4-1) with R^(1d)-M². Next, by feeding the compound (6-4-2)to the reduction reaction, a compound (6-4-3) is obtained.

Here, in the case where Y^(1d) and Y^(2d) are a hydrogen atom, thecompound (6-4-3) is fed to a reaction such as a bromination reaction,and Y^(1d) and Y^(2d) are converted into the group selected from thesubstituent group A.

Next, by a coupling reaction of the compound (6-4-3) with apredetermined amine compound, the compound (6-4-5) is obtained via thecompound (6-4-4). In the case where Z^(1d) and Z^(2d) in the compound(6-4-5) are a hydrogen atom, by feeding the compound (6-4-5) to thereaction such as the bromination reaction, the hydrogen atom can beconverted to the group selected from the substituent group A. In thecase where Z^(1d) and Z^(2d) in the compound (6-4-5) are the groupselected from the substituent group A, the group can be converted to thegroup selected from the substituent group B by a known reaction.

In Scheme 5, Y^(1e) and Y^(2e) each independently represent a hydrogenatom or the group selected from the substituent group A; Z^(1e) andZ^(2e) each independently represent a hydrogen atom or the groupselected from the substituent group A; R^(1e) and R^(2e) eachindependently represent unsubstituted or substituted alkyl group, anunsubstituted or substituted aryl group or unsubstituted or substitutedmonovalent heterocyclic group; R′ represents an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; M³ and M⁴each independently represent alkali metal such as lithium and potassiumor a group represented by -M^(II)Z^(H); M^(II) represents Mg or Zn;Z^(H) represents a halogen atom. A plurality of R^(1e) present may bethe same or different, and a plurality of R^(2e) present may be the sameor different.

In Scheme 5, first, a compound (6-5-2) is obtained by a reaction of thecompound (6-5-1) with R^(1e)-M³. Next, by feeding the compound (6-5-2),to a reaction such as methanesulfonylation, a compound (6-5-3) having aleaving group is obtained. The compound (6-5-3) may be further reactedwith R^(2e)-M⁴; by the reaction, a compound (6-5-4) is obtained.

Here, in the case where Y^(1e) and Y^(2e) are a hydrogen atom, thecompound (6-5-3) or the compound (6-5-4) is fed to a reaction such as abromination reaction, and Y^(1e) and Y^(2e) are converted into the groupselected from the substituent group A.

Next, by a coupling reaction of the compound (6-5-3) or the compound(6-5-4) with a predetermined amine compound, the compound (6-5-6) or thecompound (6-5-8) is obtained. In the case where Z^(1e) and Z^(2e) in thecompound (6-5-6) and the compound (6-5-8) are a hydrogen atom, byfeeding the compound (6-5-6) and the compound (6-5-8) to the reactionsuch as the bromination reaction, the hydrogen atom can be converted tothe group selected from the substituent group A. In the case whereZ^(1e) and Z^(2e) in the compound (6-5-6) and the compound (6-5-8) arethe group selected from the substituent group A, the group can beconverted to the group selected from the substituent group B by a knownreaction.

For example, compounds obtained by the methods described in J. Org.Chem. 2003, 68, 8715-8718 or the methods described in Journal of theChemical Society, Perkin Transactions 1: Organic and Bio-OrganicChemistry (1997), (22), 3471-3478, or compounds obtained by feeding thecompounds to the reaction such as the bromination reaction can be usedas the compound (6-1-1), the compound (6-2-1), the compound (6-3-1), thecompound (6-4-1), and the compound (6-5-1).

The compound having a stereoisomer can be synthesized bystereoselectively performing a hydrogenation reaction (hydrogenatingreaction) in Scheme 1 above as the method for obtaining a specificstereoisomer. The specific stereoisomer can also be condensed andrefined by preferential crystallization. Besides, after a stereoisomermixture is synthesized, the specific stereoisomer can be separated andrefined by chromatography.

(Composition)

The composition according to the present embodiment contains at leastone selected from the group consisting of the polymer compound, a holetransport material, an electron transport material, and a light-emittingmaterial. The composition can be suitably used in production of thelight-emitting device, in the light-emitting device to be obtained, theluminance life is excellent.

Examples of the hole transport material include polyvinylcarbazole andderivatives thereof, polysilane and derivatives thereof, polysiloxanederivatives having an aromatic amine in the side chain or the mainchain, pyrazoline derivatives, arylamine derivatives, stilbenederivatives, polyaniline and derivatives thereof, polythiophene andderivatives thereof, polypyrrole and derivatives thereof,poly(p-phenylenevinylene) and derivatives thereof, andpoly(2,5-thienylenevinylene) and derivatives thereof. Besides, examplesthereof include the hole transport materials described in JapanesePatent Application Laid-Open Nos. 63-70257, 63-175860, 2-135359,2-135361, 2-209988, 3-37992, and 3-152184.

The content of the hole transport material is preferably 1 to 500 partby weight, more preferably 5 to 200 part by weight based on 100 part byweight of the polymer compound in the composition.

Examples of the electron transport material include oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, metal complexes of8-hydroxyquinoline and derivatives thereof, polyquinoline andderivatives thereof, polyquinoxaline and derivatives thereof,polyfluorene and derivatives thereof, anthracene and derivativesthereof, and copolymers of anthracene and fluorene. Besides, examplesthereof include the electron transport materials described in JapanesePatent Application Laid-Open Nos. 63-70257, 63-175860, 2-135359,2-135361, 2-209988, 3-37992, and 3-152184.

The content of the electron transport material is preferably 1 to 500part by weight, more preferably 5 to 200 part by weight based on 100part by weight of the polymer compound in the composition.

Examples of the light-emitting material include low molecularfluorescence light-emitting materials and phosphorescence light-emittingmaterials. Examples of the light-emitting material include naphthalenederivatives; anthracene and derivatives thereof; copolymers ofanthracene and fluorene; perylene and derivatives thereof; dyes such aspolymethine dyes, xanthene dyes, coumarin dyes, and cyanine dyes; metalcomplexes having 8-hydroxyquinoline as a ligand; metal complexes having8-hydroxyquinoline derivatives as a ligand; other fluorescent metalcomplexes; aromatic amines; tetraphenylcyclopentadiene and derivativesthereof, tetraphenylbutadiene and derivatives thereof; low molecularcompound fluorescent materials such as stilbene low molecular compounds,silicon-containing aromatic low molecular compounds, oxazole lowmolecular compounds, furoxan low molecular compounds, thiazole lowmolecular compounds, tetraarylmethane low molecular compounds,thiadiazole low molecular compounds, pyrazole low molecular compounds,metacyclophane low molecular compounds, and acetylene low molecularcompounds; metal complexes such as iridium complexes and platinumcomplexes; and triplet light emitting complexes. Besides, examplesthereof include the light-emitting materials described in JapanesePatent Application Laid-Open Nos. 57-51781, 59-194393, and others.

Examples of the triplet light-emitting complex include iridium complexesin which iridium is the central metal, such as Ir(ppy)₃, Btp₂Ir(acac),FIrpic, COM-1, COM-2, COM-3, COM-4, COM-5, COM-6, COM-7, COM-8, andADS066GE available from American Dye Source, Inc.; platinum complexes inwhich platinum is the central metal, such as PtOEP; and europiumcomplexes in which europium is the central metal, such as Eu(TTA)₃phen.These triplet light-emitting complexes are represented by the followingformulas:

The content of the light-emitting material is preferably 1 to 500 partby weight, more preferably 5 to 200 part by weight based on 100 part byweight of the polymer compound in the composition.

(Liquid Composition)

The polymer compound according to the present embodiment may bedissolved or dispersed in a solvent, preferably in an organic solvent toprepare a liquid composition (solution or dispersion liquid). Such aliquid composition is also referred to as an ink or a varnish. In thecase where the liquid composition is used to form an organic film usedin the light-emitting device, it is preferable that the liquidcomposition be a solution.

In addition to the polymer compound according to the present embodiment,the liquid composition may contain at least one selected from the groupconsisting of the hole transport material, the electron transportmaterial, and the light-emitting material (namely, one embodiment of thecomposition above). Moreover, other substance may be added to the liquidcomposition unless the effects of the present invention are prevented.Examples of the other substance include an antioxidant, a viscositycontrol agent, and a surfactant.

Here, the organic solvent is not particularly limited as long as thepolymer compound according to the present embodiment is dissolved ordispersed; examples of the organic solvent include the following organicsolvents (hereinafter, referred to as a “solvent groups” in some cases).

Aromatic hydrocarbon solvents: such as toluene, xylene (isomers or amixture thereof), 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene,mesitylene (1,3,5-trimethylbenzene), ethylbenzene, propylbenzene,isopropylbenzene, butylbenzene, isobutylbenzene, 2-phenylbutane,tert-butylbenzene, pentylbenzene, neopentylbenzene, isoamylbenzene,hexylbenzene, cyclohexylbenzene, heptylbenzene, octylbenzene,3-propyltoluene, 4-propyltoluene, 1-methyl-4-propylbenzene,1,4-diethylbenzene, 1,4-dipropylbenzene, 1,4-di-tert-butylbenzene,indane, and tetralin (1,2,3,4-tetrahydronaphthalene).

Aliphatic hydrocarbon solvents: such as n-pentane, n-hexane,cyclohexane, methylcyclohexane, n-heptane, n-octane, n-nonane, n-decane,and decalin.

Aromatic ether solvents: such as anisole, ethoxybenzene, propoxybenzene,butyloxybenzene, pentyloxybenzene, cyclopentyloxybenzene,hexyloxybenzene, cyclohexyloxybenzene, heptyloxybenzene,octyloxybenzene, 2-methylanisole, 3-methylanisole, 4-methylanisole,4-ethylanisole, 4-propylanisole, 4-butylanisole, 4-pentylanisole,4-hexylanisole, diphenylether, 4-methylphenoxybenzene,4-ethylphenoxybenzene, 4-propylphenoxybenzene, 4-butylphenoxybenzene,4-pentylphenoxybenzene, 4-hexylphenoxybenzene, 4-phenoxytoluene,3-phenoxytoluene, 1,3-dimethoxybenzene, 2,6-dimethylanisole,2,5-dimethylanisole, 2,3-dimethylanisole, and 3,5-dimethylanisole.

Aliphatic ether solvents: such as tetrahydrofuran, dioxane, anddioxolane.

Ketone solvents: such as acetone, methyl ethyl ketone, methyl isobutylketone, cyclohexanone, and acetophenone.

Ester solvents: such as ethyl acetate, butyl acetate, methyl benzoate,and ethyl cellosolve acetate.

Chlorinated solvents: such as methylene chloride, chloroform,1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, ando-dichlorobenzene.

Alcohol solvents: methanol, ethanol, propanol, isopropanol,cyclohexanol, and phenol.

Polyhydric alcohols and derivatives thereof: such as ethylene glycol,ethylene glycol monobutyl ether, ethylene glycol monoethyl ether,ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol,diethoxymethane, triethylene glycol monoethyl ether, glycerol, and1,2-hexanediol.

Aprotic polar solvents: such as dimethylsulfoxide,N-methyl-2-pyrrolidone, N,N-dimethylformamide, andN,N-dimethylacetoamide.

These organic solvents may be used alone, or two or more thereof may beused as a mixed solvent. In the case where the mixed solvent is used, itis preferable that two or three or more of the solvents in the solventgroups be used in combination; several solvents from the same solventgroup described above may be used in combination, or one or moresolvents from different solvent groups may be used in combination. Thecomposition ratio can be determined considering the physical propertiesof the solvents, the solubility of the polymer compound, and the like.

Preferable examples in the case where several solvents are selected fromthe same solvent group and used in combination include several solventsfrom the aromatic hydrocarbon solvents, and several solvents from thearomatic ether solvents.

Preferable examples in the case where one or more solvents are selectedfrom different solvent groups and used in combination include thefollowing combinations:

the aromatic hydrocarbon solvent and the aliphatic hydrocarbon solvent;

the aromatic hydrocarbon solvent and the aromatic ether solvent;

the aromatic hydrocarbon solvent and the aliphatic ether solvents;

the aromatic hydrocarbon solvent and the aprotic polar solvent; and

the aromatic ether solvent and the aprotic polar solvent.

A single solvent or the mixed organic solvent can be added to water.

Among these organic solvents, a single solvent or mixed solventcontaining one or more organic solvents having a structure including abenzene ring, a melting point of 0° C. or less, and a boiling point of100° C. or more is preferable; among these, a single solvent or mixedsolvent containing one or more of the aromatic hydrocarbon solvents andthe aromatic ether solvents are particularly preferable from theviewpoint of viscosity and good film forming properties.

These organic solvents can be used alone, or two or more thereof can beused in combination as a mixed solvent; since the film formingproperties can be controlled, it is preferable that the mixed solvent beused. When necessary, the organic solvent may be refined by a methodsuch as washing, distillation, and contacting with an adsorbent, andused.

According to the liquid composition, the organic film containing thepolymer compound according to the present embodiment can be easilyproduced. Specifically, the liquid composition is applied onto asubstrate, and the organic solvent is distilled away by heating, sendingair, reducing pressure, or the like; thereby, the organic filmcontaining the polymer compound according to the present embodiment isobtained. In the distillation of the organic solvent, the condition canbe changed depending on the organic solvent to be used; examples of thecondition include an atmosphere temperature of 50 to 150° C. (heating)or a reduced pressure atmosphere of approximately 10⁻³ Pa.

As the application, an application method such as a spin coating method,a casting method, a microgravure method, a gravure coating method, a barcoating method, a roll coating method, a wire bar coating method, a dipcoating method, a slit coating method, a capillary coating method, aspray coating method, a screen printing method, a flexographic printingmethod, an offset printing method, an inkjet print method, and a nozzlecoating method can be used.

A suitable viscosity of the liquid composition varies depending on theprinting method; the viscosity at 25° C. is preferably 0.5 to 1000mPa·s, and more preferably 0.5 to 500 mPa·s. In the case where theliquid composition is passed through an ejecting apparatus as in theinkjet print method, to prevent clogging and curved flight of inkdroplets during ejection, the viscosity at 25° C. is preferably 0.5 to50 mPa·s, and more preferably 0.5 to 20 mPa·s. The concentration of thepolymer compound according to the present embodiment in the liquidcomposition is not limited; it is preferable that the concentration be0.01 to 10% by weight, and it is more preferable that the concentrationbe 0.1 to 5% by weight.

(Organic Film)

The organic film according to the present embodiment contains thepolymer compound. The organic film according to the present embodimentcan be easily produced from the liquid composition as above.

The organic film according to the present embodiment can be suitablyused as a light-emitting layer in the light-emitting device describedlater. The organic film according to the present embodiment can also besuitably used for an organic semiconductor device. Because the organicfilm according to the present embodiment contains the polymer compound,the luminance life of the light-emitting device is excellent in the casewhere the organic film is used as the light-emitting layer in thelight-emitting device

(Light-Emitting Device)

The light-emitting device according to the present embodiment has theorganic film.

Specifically, the light-emitting device according to the presentembodiment has an anode, a cathode, and a layer existing between theanode and the cathode and containing the polymer compound. Here, it ispreferable that the layer containing the polymer compound be a layerformed of the organic film, and the layer function as the light-emittinglayer. Hereinafter, the case where the layer containing the polymercompound functions as the light-emitting layer will be exemplified aspreferable one embodiment.

Examples of the light-emitting device according to the presentembodiment include light-emitting devices having the followingstructures (a) to (d). The symbol “/” designates that the layers beforeand after the symbol are adjacent and laminated (for example,“anode/light-emitting layer” designates that the anode and thelight-emitting layer are adjacent and laminated).

(a) anode/light-emitting layer/cathode

(b) anode/hole transport layer/light-emitting layer/cathode

(c) anode/light-emitting layer/electron transport layer/cathode

(d) anode/hole transport layer/light-emitting layer/electron transportlayer/cathode

The light-emitting layer is a layer having a light emission function.

The hole transport layer is a layer having a function to transportholes.

The electron transport layer is a layer having a function to transportelectrons.

The hole transport layer and the electron transport layer arecollectively referred to as a charge transport layer in some cases.

The hole transport layer adjacent to the light-emitting layer isreferred to as an interlayer layer in some cases.

Lamination of the layers and film formation can be performed using asolution containing components that form each of the layers. Inlamination and film forming from a solution, an application method suchas a spin coating method, casting method, a microgravure coating method,a gravure coating method, a bar coating method, a roll coating method, awire bar coating method, a dip coating method, a slit coating method, acapillary coating method, a spray coating method, a screen printingmethod, a flexographic printing method, an offset printing method, aninkjet print method, and a nozzle coating method can be used.

The thickness of the light-emitting layer may be selected such that thedriving voltage, the light emission efficiency, and the luminance lifeare proper values; the thickness is usually 1 nm to 1 μm, preferably 2nm to 500 nm, and still more preferably 5 nm to 200 nm.

It is preferable that the hole transport layer contain the holetransport material. Film formation of the hole transport layer may beperformed by any method; in the case where the hole transport materialis a polymer compound, it is preferable that film formation be performedfrom the solution containing the hole transport material; in the casewhere the hole transport material is a low-molecular compound, it ispreferable that film formation be performed from a mixed solutioncontaining a polymer binder and the hole transport material. As the filmforming method, the same method as the application method above can beused.

As the polymer binder that can be mixed with the hole transportmaterial, a compound that does not extremely inhibit chargetransportation and whose absorption of visible light is not strong ispreferable. Examples of the polymer binder include polycarbonate,polyacrylate, polymethylacrylate, polymethylmethacrylate, polystyrene,polyvinyl chloride, and polysiloxane.

The thickness of the hole transport layer may be selected such that thedriving voltage, the light emission efficiency, and the luminance lifeare proper values; the thickness is usually 1 nm to 1 μm, preferably 2nm to 500 nm, and still more preferably 5 nm to 200 nm.

It is preferable that the electron transport layer contain the electrontransport material above. The film formation of the electron transportlayer may be performed by any method; in the case where the electrontransport material is a polymer compound, a method of forming a filmfrom a solution containing the electron transport material, and a methodof melting the electron transport material and forming a film or thelike are preferable. In the case where the electron transport materialis a low-molecular compound, a method of forming a film using a powderof the electron transport material by a vacuum evaporation method, amethod of forming a film from a solution containing the electrontransport material, and a method of melting the electron transportmaterial and forming a film or the like are preferable. Examples of themethod of forming a film from a solution containing the electrontransport material can include the same method as the application methodabove. A polymer binder may be contained in the solution.

As the polymer binder that can be mixed with the electron transportmaterial, a compound that does not extremely inhibit chargetransportation and whose absorption of visible light is not strong ispreferable. Examples of the polymer binder includepoly(N-vinylcarbazole), polyaniline and derivatives thereof,polythiophene and derivatives thereof, poly(para-phenylenevinylene) andderivatives thereof, poly(2,5-thienylenevinylene) and derivativesthereof, polycarbonate, polyacrylate, polymethylacrylate, polymethylmethacrylate, polystyrene, polyvinyl chloride, and polysiloxane.

The thickness of the electron transport layer may be selected such thatthe driving voltage, the light emission efficiency, and the luminancelife are proper values; the thickness is usually 1 nm to 1 μm,preferably 2 nm to 500 nm, and still more preferably 5 nm to 200 nm.

Among the charge transport layers provided adjacent to an electrode, acharge transport layer having a function to improve charge injectionefficiency from the electrode and an effect of reducing the drivingvoltage of the device is particularly referred to as a charge injectionlayer (hole injection layer, electron injection layer) in some cases. Inorder to improve adhesion of the electrode and injection of charges fromthe electrode, the charge injection layer or insulating layer may beprovided adjacent to the electrode; in order to improve adhesion of theinterface and prevention of mixing, a thin buffer layer may be insertedinto the interface between the charge transport layer and thelight-emitting layer. The order and the number of the layers to belaminated and the thicknesses of the layers may be selected consideringthe light emission efficiency and luminance life.

Examples of the light-emitting device in which the charge injectionlayer is provided include light-emitting devices having the followingstructures (e) to (p):

(e) anode/charge injection layer/light-emitting layer/cathode

(f) anode/light-emitting layer/charge injection layer/cathode

(g) anode/charge injection layer/light-emitting layer/charge injectionlayer/cathode

(h) anode/charge injection layer/hole transport layer/light-emittinglayer/cathode

(i) anode/hole transport layer/light-emitting layer/charge injectionlayer/cathode

(j) anode/charge injection layer/hole transport layer/light-emittinglayer/charge injection layer/cathode

(k) anode/charge injection layer/light-emitting layer/charge transportlayer/cathode

(l) anode/light-emitting layer/electron transport layer/charge injectionlayer/cathode

(m) anode/charge injection layer/light-emitting layer/electron transportlayer/charge injection layer/cathode

(n) anode/charge injection layer/hole transport layer/light-emittinglayer/charge transport layer/cathode

(o) anode/hole transport layer/light-emitting layer/electron transportlayer/charge injection layer/cathode

(p) anode/charge injection layer/hole transport layer/light-emittinglayer/electron transport layer/charge injection layer/cathode

Examples of the charge injection layer include (I) a layer containing aconductive polymer, (II) a layer provided between the anode and the holetransport layer and containing a material having an ionization potentialof a middle value between the anode material in the anode and the holetransport material in the hole transport layer, and (III) a layerprovided between the cathode and the electron transport layer and alayer containing a material having an electron affinity force of amiddle value between the cathode material in the cathode and theelectron transport material in the electron transport layer.

In the case where the charge injection layer is (I) the layer containinga conductive polymer, it is preferable that the electric conductivity ofthe conductive polymer be 10⁻⁵ S/cm to 10³ S/cm; in order to reduce theleak current between light-emitting pixels, it is more preferable thatthe electric conductivity of the conductive polymer be 10⁻⁵ S/cm to 10²S/cm, and it is still more preferable that the electric conductivity ofthe conductive polymer be 10⁻⁵ S/cm to 10¹ S/cm. In order to satisfy therange, the conductive polymer may be doped with a proper amount of ion.

The kind of ions to be doped with is an anion for a hole injectionlayer, and a cation for the electron injection layer. Examples of theanion include polystyrenesulfonic acid ion, alkylbenzenesulfonic acidion, and camphorsulfonic acid ion. Examples of the cation includelithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

It is preferable that the thickness of the charge injection layer be 1to 100 nm, and it is more preferable that the thickness of the chargeinjection layer be 2 to 50 nm.

The conductive polymer may be selected according to the relationshipwith the electrode and the material of the adjacent layer; examplesthereof include conductive polymers such as polyaniline and derivativesthereof, polythiophene and derivatives thereof, polypyrrole andderivatives thereof, polyphenylenevinylene and derivatives thereof,polythienylenevinylene and derivatives thereof, polyquinoline andderivatives thereof, polyquinoxaline and derivatives thereof, andpolymers including an aromatic amine structure in the main chain or sidechain. Examples of the charge injection layer include metalphthalocyanines (such as copper phthalocyanine) and layers containingcarbon or the like.

The insulating layer is a layer having a function to facilitateinjection of charges. The thickness of the insulating layer is usually0.1 to 20 nm, preferably 0.5 to 10 nm, and more preferably 1 to 5 nmExamples of a material used as the insulating layer include metalfluorides, metal oxides, and organic insulating materials.

Examples of the light-emitting device in which the insulating layer isprovided include light-emitting devices having the following structures(q) to (ab):

(q) anode/insulating layer/light-emitting layer/cathode

(r) anode/light-emitting layer/insulating layer/cathode

(s) anode/insulating layer/light-emitting layer/insulating layer/cathode

(t) anode/insulating layer/hole transport layer/light-emittinglayer/cathode

(u) anode/hole transport layer/light-emitting layer/insulatinglayer/cathode

(v) anode/insulating layer/hole transport layer/light-emittinglayer/insulating layer/cathode

(w) anode/insulating layer/light-emitting layer/electron transportlayer/cathode

(x) anode/light-emitting layer/electron transport layer/insulatinglayer/cathode

(y) anode/insulating layer/light-emitting layer/electron transportlayer/insulating layer/cathode

(z) anode/insulating layer/hole transport layer/light-emittinglayer/electron transport layer/cathode

(aa) anode/hole transport layer/light-emitting layer/electron transportlayer/insulating layer/cathode

(ab) anode/insulating layer/hole transport layer/light-emittinglayer/electron transport layer/insulating layer/cathode

It is preferable that the light-emitting device according to the presentembodiment have a substrate adjacent to the anode or the cathode. As thesubstrate, a substrate whose shape and properties do not change when theelectrode and the layers are formed are preferable; examples thereofinclude substrates made of glass, plastics, polymer films, silicon, andthe like. In the case of the non-transparent substrate, it is preferablethat an electrode opposite to an electrode that the substrate contactsbe transparent or semi-transparent.

In the light-emitting device according to the present embodiment,usually, at least one of the electrodes composed of the anode and thecathode is transparent or semi-transparent; it is preferable that theanode be transparent or semi-transparent.

As the material for the anode, conductive metal oxide films,semi-transparent metal films, and the like are used. Specifically, filmsproduced using a conductive inorganic compound such as composite oxidesformed of indium oxide, zinc oxide, tin oxide, and indium tin oxide(ITO) and composite oxides formed of indium zinc oxide, NESA, gold,platinum, silver, copper, and the like are used. As the anode, anorganic transparent conductive film formed of polyaniline andderivatives thereof, polythiophene and derivatives thereof, and the likemay be used. In order to facilitate injection of charges, a layer formedof a phthalocyanine derivative, a conductive polymer, carbon, or thelike, or a layer formed of a metal oxide, a metal fluoride, an organicinsulating material, or the like may be provided on the anode.

Examples of the method of producing the anode include a vacuumevaporation method, a sputtering method, an ion plating method, and aplating method.

The thickness of the anode can be selected considering lighttransmittance and electric conductivity; the thickness is usually 10 nmto 10 μm, preferably 20 nm to 1 μm, and still more preferably 30 nm to500 nm.

As the material for the cathode, a material whose work function is smallis preferable; a metal such as lithium, sodium, potassium, rubidium,cesium, beryllium, magnesium, calcium, strontium, barium, aluminum,scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium,terbium, and ytterbium, an alloy containing two or more of the metals,an alloy containing one or more of the metals and one or more of gold,silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten,and tin, graphite or a graphite interlayer compound, and the like areused.

As the method of producing the cathode, a vacuum evaporation method, asputtering method, a lamination method for thermally pressing a metalfilm, and the like are used.

The thickness of the cathode can be selected considering electricconductivity and durability; the thickness is usually 10 nm to 10 μm,preferably 20 nm to 1 μm, and still more preferably 50 nm to 500 nm.

A layer formed of a conductive polymer or a layer formed of a metaloxide, a metal fluoride, an organic insulating material, or the like maybe provided between the cathode and the light-emitting layer or betweenthe cathode and the electron transport layer; after production of thecathode, a protective layer for protecting the light-emitting device maybe attached. In order to use the light-emitting device stably for a longtime, it is preferable that a protective layer and/or a protective coverbe attached to protect the light-emitting device from the outside.

As the protective layer, resins, metal oxides, metal fluorides, metalborides, and the like can be used. As the protective cover, a glassplate, a plastic plate whose surface is subjected to a low moisturepermeation treatment; a method of bonding the protective cover to andevice substrate with a thermosetting resin or a photocurable resin issuitably used. If a space is kept using a spacer, the device can beeasily prevented from being scratched. If an inert gas such as nitrogenand argon is sealed in the space, oxidation of the cathode can beprevented; further, by providing a desiccant such as barium oxide insideof the space, suppression in moisture adsorbed during the productionstep damaging the device is easy.

FIG. 1 is a schematic sectional view showing one embodiment of alight-emitting device according to the present invention (light-emittingdevice having the structure (p)). The light-emitting device 100 shown inFIG. 1 has a substrate 10, an anode 11 formed on the substrate 10, ahole injection layer 12, a hole transport layer 13, a light-emittinglayer 14, an electron transport layer 15, an electron injection layer16, and a cathode 17. The anode 11 is provided on the substrate 10 so asto contact the substrate 10; on a side of the anode 11 opposite to thesubstrate 10, the hole injection layer 12, the hole transport layer 13,the light-emitting layer 14, the electron transport layer 15, theelectron injection layer 16, and the cathode 17 are laminated in thisorder.

FIG. 2 is a schematic sectional view showing another embodiment of thelight-emitting device according to the present invention (light-emittingdevice having the structure (h)). The light-emitting device 110 shown inFIG. 2 has a substrate 10, an anode 11 formed on the substrate 10, ahole injection layer 12, a hole transport layer 13, a light-emittinglayer 14, and a cathode 17. The anode 11 is provided on the substrate 10so as to contact the substrate; on a side of the anode 11 opposite tothe substrate 10, the hole injection layer 12, the hole transport layer13, the light-emitting layer 14, and the cathode 17 are laminated inthis order.

The light-emitting device containing the polymer compound according tothe present embodiment is useful for surface lighting sources such ascurved surface lighting sources and flat surface lighting sources (suchas lighting); and display devices such as segment display devices, dotmatrix display devices (such as dot matrix flat displays), and liquidcrystal display devices (for example, liquid crystal display devices andbacklights of liquid crystal displays), for example. The polymercompound according to the present embodiment is suitable for thematerial used in production of these; besides, the polymer compoundaccording to the present embodiment is also suitable for dyes for alaser, a material for a conductive film such as materials for an organicsolar cell, organic semiconductors for an organic transistor, conductivefilms, organic semiconductor films, a light-emittable film material thatemits fluorescence, a material for polymer field-effect transistors, andthe like.

In order to obtain a planar light emission using the light-emittingdevice according to the present embodiment, a planar anode and cathodemay be disposed so as to be layered. In order to obtain a patternedlight emission, a method in which a mask in which a patterned window isprovided is provided on the surface of the planar light-emitting device,and a method in which one of the anode and the cathode or both of theelectrode are formed to be patterned are used. A pattern is formed byany of these methods, and some of electrodes are arranged to be capableof being turned ON/OFF independently; thereby, a segment display deviceon which numerals, letters, simple symbols, and the like can bedisplayed is obtained.

Further, to obtain a dot matrix display device, the anode and thecathode both may be formed in a strip form and arranged intersectingperpendicular to each other. Partial color display and multicolordisplay are enabled by a method for applying polymer compounds of aplurality of different light-emitting colors, or a method using a colorfilter or a fluorescence conversion filter. The dot matrix displaydevice can be passively driven, or may be actively driven in combinationwith a TFT or the like. These display devices can be used as displaydevices for computers, televisions, mobile terminals, mobile phones, carnavigation systems, view finders for video cameras, and the like.

FIG. 3 is a schematic sectional view showing one embodiment of thesurface lighting source according to the present invention. The surfacelighting source 200 shown in FIG. 3 includes a substrate 20, an anode21, a hole injection layer 22, a light-emitting layer 23, a cathode 24,and a protective layer 25. The anode 21 is provided on the substrate 20so as to contact the substrate 20; on a side of the anode 21 opposite tothe substrate 20, the hole injection layer 22, the light-emitting layer23, and the cathode 24 are laminated in this order. The protective layer25 is formed so as to cover all the anode 21, the charge injection layer22, the light-emitting layer 23, and the cathode 24 formed on thesubstrate 20 and contact the substrate 20 at the end. The polymercompound is contained in the light-emitting layer 23.

The surface lighting source 200 shown in FIG. 3 is configured to furtherhave a plurality of light-emitting layers other than the light-emittinglayer 23, and can be formed as a color display device by using a redlight-emitting material, a blue light-emitting material, and a greenlight-emitting material for each of the light-emitting layers andcontrolling drive of the light-emitting layers.

EXAMPLES

Hereinafter, the present invention will be more specifically describedusing Examples, but the present invention will not be limited toExamples.

The polystyrene-equivalent number-average molecular weight andweight-average molecular weight of the polymer compound were determinedusing a gel permeation chromatograph (GPC) (made by SHIMADZUCorporation, trade name: LC-10Avp) on the following measurementcondition.

<Measurement Condition>

The polymer compound to be measured was dissolved in tetrahydrofuransuch that the concentration was approximately 0.05% by weight, and 10 μLof the solution was injected to the GPC. Tetrahydrofuran was used as amobile phase for the GPC, and flowed at a flow rate of 2.0 mL/min. As acolumn, a PLgel MIXED-B (made by Polymer Laboratories Ltd.) was used. Asa detector, a differential refractive index detector (made by SHIMADZUCorporation, trade name: RID-10A) was used.

Measurement of NMR was performed by dissolving 5 to 20 mg of ameasurement sample in approximately 0.5 mL of an organic solvent andusing an NMR (made by Varian, Inc., trade name: INOVA300).

Measurement of LC-MS was performed by the following method. Ameasurement sample was dissolved in a proper organic solvent (such aschloroform, tetrahydrofuran, ethyl acetate, and toluene) such that theconcentration was 1 to 10 mg/mL, measured with an LC-MS (made by AgilentTechnologies, Inc., trade name: 1100LCMSD), and analyzed. As a mobilephase for the LC-MS, ion exchange water, acetonitrile, tetrahydrofuran,or a mixed liquid thereof was used, and when necessary acetic acid wasadded. As a column, an L-column 2 ODS (3 μm) (made by ChemicalsEvaluation and Research Institute, Japan, inner diameter: 4.6 mm,length: 250 mm, particle diameter: 3 μm) was used.

Example 1: Synthesis of Compound 5

(Synthesis of Compound 2)

First, using Compound 1, Compound 2 was synthesized as follows.

Compound 1 (4.5 g) and ethylene glycol (180 g) were placed in a 500 mLfour-necked flask including a stirrer, and the gas inside of the flaskwas replaced with argon. Hydrazine monohydrate (3.2 g) and potassiumhydroxide (4.3 g) were placed in the flask, and the temperature wasraised to 180° C.; stirring was performed at the temperature for 28hours while the temperature was kept. The reaction solution was cooledto room temperature, and water was added; then, a solid wasprecipitated. The solid was filtered, recovered, and dried by reducingpressure at room temperature; thereby, 3.9 g of Compound 2 was obtainedas a white solid.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 1.35-1.72 (4H, m), 1.89-2.24 (8H, m),7.10-7.46 (6H, m), 7.90 (2H, d).

(Synthesis of Compound 3)

Next, using Compound 2, Compound 3 was synthesized as follows.

The gas inside of a 100 mL four-necked flask including a stirrer wasreplaced with argon, and Compound 2 (3.7 g), chloroform (45 g), andtrifluoroacetic acid (7.5 mL) were added. The entire four-necked flaskwas shielded from light, and a mixture of bromine (5.7 g) and chloroform(11.2 g) was added at room temperature. Stirring was performed at roomtemperature for 2.5 hours while the temperature was kept, and a 10% byweight sodium sulfite aqueous solution (20 g) was added. An aqueouslayer was separated from the reaction solution, and an organic layer waswashed with water, a 10% by weight dipotassium hydrogenphosphate aqueoussolution, and water in this order. The obtained organic layer was driedwith magnesium sulfate, and filtered; the filtrate was condensed toobtain a crude product. The crude product was recrystallized with amixed liquid of toluene and methanol; the obtained solid was dissolvedin chloroform, and refined using a silica gel column (developing solventof toluene/hexane). The obtained solution was condensed, and activatedcarbon (3 g) was added; stirring was performed at 65° C. for 0.5 hourswhile the temperature was kept. The solution was filtered at thetemperature with a filter precoated with celite to obtain a filtrate anda residue. Next, the residue was washed with toluene several times toobtain a washing liquid. Here, the filtrate and the washing liquidobtained by washing several times were added, and partially condensed toobtain a toluene solution. Hexane was added to the toluene solution, andrecrystallized; thereby, 3.6 g of Compound 3 was obtained as a whitesolid.

LC-MS (ESI, positive): [M+H]⁺417.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 1.38-1.76 (4H, m), 1.85-2.24 (8H, m),7.33 (2H, d), 7.50 (2H, s), 7.70 (2H, d).

(Synthesis of Compound 4)

Next, using Compound 3, Compound 4 was synthesized as follows.

N-phenyl-N-(4-tert-butyl)-2,6-dimethyl phenyl amine (24.3 g),tris(dibenzylidene acetone)dipalladium(0) (1.99 g),tri-tert-butylphosphonium tetrafluoroborate (2.53 g), and sodiumtert-butoxide (12.6 g) were placed in a 500 mL four-necked flaskincluding a stirrer, and the gas inside of the flask was replaced withnitrogen. Toluene (100 mL) and tert-butanol (9 mL) were placed in theflask, and a mixture of Compound 3 (18.2 g) and toluene (170 mL) wasdropped. Then, the temperature was raised to a reflux temperature, andstirring was performed for 2 hours while the temperature was kept.

The reaction solution was cooled to room temperature, and water wasadded; the reaction solution was filtered with a filter precoated withcelite. The residue was washed with toluene, the aqueous layer wasseparated from the filtrate, and the organic layer was washed withwater. The obtained organic layer was condensed to obtain a crudeproduct. The crude product was refined using a silica gel column(developing solvent of a hexane/toluene mixed liquid). The obtainedsolution was condensed, and recrystallized with a mixed liquid ofisopropanol and toluene to obtain 30.6 g of Compound 4 as a white solid.

(Synthesis of Compound 5)

Next, using Compound 4, Compound 5 was synthesized as follows.

The gas inside of a 1 L four-necked flask including a stirrer wasreplaced with nitrogen; Compound 4 (30.1 g), N,N-dimethyl formamide (36mL), chlorobenzene (360 mL), and chloroform (100 mL) were placed in theflask, and cooling was performed to 10° C. The flask was shielded fromlight, and N-bromosuccinimide (NBS) (14.2 g) was divided into severalportions and added at 10° C. Stirring was performed at the temperaturefor 4 hours while the temperature was kept, and water was added; next, asaturated sodium sulfite aqueous solution was added until the color ofbromine disappeared. The temperature was raised to room temperature;then, chloroform was added to the obtained solution, and the aqueouslayer was separated. The organic layer was washed with water twice, andcondensed to obtain a crude product. The crude product was dissolved intoluene; the temperature was raised to 65° C., and silica gel (75 g) andactivated carbon (2 g) were added; stirring was performed for 30 minuteswhile the temperature was kept. The solution was filtered with a filterprecoated with silica gel, and the residue was washed with toluene.Isopropanol was added to the obtained toluene solution to performrecrystallization; then, recrystallization was further performed with amixed liquid of toluene and isopropanol to obtain 29.8 g of Compound 5as a white solid.

LC-MS (APCI, positive): [M+H]⁺919.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 1.11-1.63 (22H, m), 1.80-2.08 (20H, m),6.53-6.70 (2H, br), 6.75-6.90 (4H, m), 7.05-7.36 (10H, m), 7.50-7.66(2H, br).

Example 2: Synthesis of Compound 10

(Synthesis of Compound 6)

First, using Compound 1, Compound 6 was synthesized as follows.

(wherein the wavy line indicates that the compound having the wavy lineis a geometric isomer mixture).

n-Heptyltriphenylphosphonium bromide (115.0 g) was placed in a 1 Lfour-necked flask including a stirrer, and the gas inside of the flaskwas replaced with argon. Toluene (375 g) was placed in the flask, andcooling was performed to 5° C. or less. Potassium tert-butoxide (29.2 g)was placed in the flask, and the temperature was raised to roomtemperature; then, stirring was performed at room temperature for 3hours while the temperature was kept. Compound 1 (15.0 g) was added to ared slurry produced during the reaction solution, and stirring wasperformed at room temperature for 12 hours while the temperature waskept. Acetic acid (10.0 g) was added to the reaction solution, andstirring was performed for 15 minutes; the reaction solution wasfiltered to obtain a filtrate and a residue. Next, the residue waswashed with toluene several times to obtain a washing liquid. Here, thefiltrate and the washing liquid obtained by washing several times wereadded, and condensed; when hexane was added, a slurry was produced; theslurry was stirred at 50° C. for 1 hour while the temperature was kept.The obtained mixture was cooled to room temperature, and filtered toobtain a filtrate and a residue. Next, the residue was washed withhexane several times to obtain a washing liquid. Here, the filtrate andthe washing liquid obtained by washing several times were added, andcondensed to obtain a crude product. The crude product was refined usinga silica gel column (developing solvent of hexane) to obtain 21.7 g ofCompound 6 as a colorless transparent liquid.

LC-MS (ESI, positive, KCl added): [M+K]⁺491.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 0.87 (6H, t), 1.20-1.36 (16H, m),1.82-1.97 (4H, m), 2.57-2.81 (8H, m), 5.20 (2H, br), 7.23-7.32 (4H, m),7.41-7.48 (2H, m), 7.87-7.90 (2H, m).

(Synthesis of Compound 7)

Next, using Compound 6, Compound 7 was synthesized as follows.

(wherein the wavy line indicates that the compound having the wavy lineis a geometric isomer mixture; * indicates that a carbon atom to which *is attached is an asymmetric carbon atom).

Compound 6 (21.7 g) was placed in a 1 L four-necked flask including astirrer, and ethyl acetate (152.4 g) and ethanol (151.6 g) were placedin the flask; the gas inside of the flask was replaced with nitrogen. 5%by weight Pd/C (a product containing approximately 50% by weight ofwater) (4.3 g) was added; then, the gas inside of the flask was replacedwith hydrogen; under a hydrogen atmosphere, stirring was performed at40° C. for 27 hours while the temperature was kept. Cooling wasperformed to room temperature, and filtration was performed with afilter precoated with celite to obtain a filtrate and a residue. Next,the residue was washed with ethyl acetate several times to obtain awashing liquid. Here, the filtrate and the washing liquid obtained bywashing several times were added, and condensed to obtain a crudeproduct. The crude product was refined using a silica gel column(developing solvent of hexane) to obtain 21.7 g of Compound 7 as acolorless transparent liquid.

LC-MS (APPI, positive): [M]⁺456.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 0.66-0.98 (6H, m), 1.00-2.22 (34H, m),7.13-7.50 (6H, m), 7.80-7.98 (2H, m).

(Synthesis of Compound 8)

Next, using Compound 7, Compound 8 was synthesized as follows.

(wherein * indicates that a carbon atom to which * is attached is anasymmetric carbon atom).

Compound 7 (21.7 g), chloroform (261.1 g), and trifluoroacetic acid (44g) were placed in a 500 mL four-necked flask including a stirrer, andthe gas inside of the flask was replaced with argon. The entirefour-necked flask was shielded from light, and a mixture of bromine(19.0 g) and chloroform (65.3 g) was dropped into the flask at roomtemperature over 15 minutes; then, the temperature was raised to 35° C.Stirring was performed at 35° C. for 7 hours while the temperature waskept; then, cooling was performed to 15° C. or less. A 10% by weightsodium sulfite aqueous solution (109 g) was added to the reactionsolution, and the temperature was raised to room temperature. An aqueouslayer was separated from the reaction solution, and an organic layer waswashed with water, a 5% by weight sodium hydrogencarbonate aqueoussolution, and water in this order. The obtained organic layer was driedwith magnesium sulfate, and filtered; the filtrate was condensed toobtain a crude product. The crude product was recrystallized twice witha mixed liquid of ethanol and hexane. The obtained solid was dissolvedin hexane, and refined using a silica gel column (developing solvent ofhexane); activated carbon (2.1 g) was added to the obtained hexanesolution, and the solution was stirred at 45° C. for 1 hour while thetemperature was kept. The obtained mixture was cooled to roomtemperature, and filtered with a filter precoated with celite to obtaina filtrate and a residue. Next, the residue was washed with hexaneseveral times to obtain a washing liquid. Here, the filtrate and thewashing liquid obtained by washing several times were added, andpartially condensed to obtain a hexane solution. Ethanol was added tothe hexane solution, and recrystallization was performed to obtain 18.8g of Compound 8 as a white solid.

LC-MS (ESI, negative, KCl added): [M+Cl]⁻648.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 0.66-0.98 (6H, m), 1.00-2.20 (34H, m),7.22-7.78 (6H, m).

From the ¹H-NMR measurement result, it was found out that Compound 8 isa mixture of isomers with different stereochemistry (9a:9b:9c=51:39:10)(molar ratio).

(Synthesis of Compound 9)

Next, using Compound 8, Compound 9 was synthesized as follows.

(wherein * indicates that a carbon atom to which * is attached is anasymmetric carbon atom).

N-phenyl-N-(4-tert-butyl)-2,6-dimethyl phenyl amine (4.53 g),tris(dibenzylidene acetone)dipalladium(0) (0.37 g), tri-tert-butylphosphonium tetrafluoroborate (0.71 g), and sodium tert-butoxide (2.35g) were placed in a 500 mL four-necked flask including a stirrer, andthe gas inside of the flask was replaced with argon. Xylene (50 mL) andtert-butanol (10 mL) were added to the flask, and a mixture of Compound8 (5.00 g) and xylene (50 mL) was dropped. Then, the temperature wasraised to a reflux temperature, and stirring was performed for 3 hourswhile the temperature was kept. The reaction solution was cooled to roomtemperature, and water and toluene were added; the reaction solution wasstirred at room temperature; then, an aqueous layer was separated, andan organic layer was washed with a saturated sodium chloride aqueoussolution. Sodium sulfate was added to the obtained organic layer, andfiltration and then condensation were performed to obtain a crudeproduct. The crude product was refined using a silica gel column(developing solvent of hexane/toluene mixed liquid). The obtainedsolution was condensed, and recrystallized with a mixed liquid ofisopropanol and toluene to obtain 5.0 g of Compound 9 as a white solid.

(Synthesis of Compound 10)

Next, Compound 10 was synthesized using Compound 9 as follows.

(wherein * indicates that a carbon atom to which * is attached is anasymmetric carbon atom).

The gas inside of a 1 L four-necked flask including a stirrer wasreplaced with argon; Compound 9 (4.25 g), N,N-dimethyl formamide (4 mL),and chlorobenzene (20 mL) were placed in the flask, and cooling wasperformed to 10° C. The flask was shielded from light, andN-bromosuccinimide (NBS) (1.59 g) was divided into several portions andadded at 10° C. Then, the temperature was raised to room temperature,and stirring was performed for 17 hours while the temperature was kept;then, water was added; next, a saturated sodium sulfite aqueous solutionwas added until the color of bromine disappeared. The temperature wasraised to room temperature, hexane was added to the reaction solution,and an aqueous layer was separated. The organic layer was washed oncewith water, and once with a saturated sodium chloride aqueous solution,and condensed to obtain a crude product. The crude product was refinedusing a silica gel column (developing solvent of hexane/toluene mixedliquid). The obtained solution was condensed, and recrystallized withisopropanol to obtain 3.8 g of Compound 10 as a white solid.

LC-MS (APCI, positive): [M+H]⁺1115.

¹H-NMR (CDCl₃, 300 MHz) δ (ppm): 0.71-0.98 (6H, m), 0.98-2.31 (64H, m),6.39-7.86 (18H, m).

From the ¹H-NMR and HPLC measurement results, it was found out thatCompound 10 is a mixture of isomers with different stereochemistry(10a:10b:10c=49:46:5) (molar ratio).

Synthesis Example 1: Synthesis of Compound 13

(Synthesis of Compound 11)

Using 1,5-naphthyl bis(trifluoromethanesulfonate), Compound 11 wassynthesized as follows.

Under a nitrogen atmosphere, 1,5-naphthyl bis(trifluoromethanesulfonate)(25.0 g), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethylene adduct (0.24 g), and tert-butylmethylether (410mL) were prepared, 2-ethylhexylmagnesium bromide (173 mL of a 1 mol/Ldiethyl ether solution) was dropped at 10° C. or less, and stirring wasperformed at room temperature for 4 hours. After the reaction wascompleted, the reaction solution was poured to a mixed liquid of water(500 ml) and 2 N hydrochloric acid (100 ml), and extracted with ethylacetate; the obtained organic layer was washed with a sodium chlorideaqueous solution; the washed organic layer was dried with magnesiumsulfate, and the solvent was distilled away under reduced pressure. Theresidue was refined by silica gel column chromatography (developingsolvent of hexane) to obtain 21.3 g of Compound 11 as a light yellow oilproduct.

LC-MS (ESI, positive): [M^(+])353.

¹H-NMR (300 MHz, CDCl₃) δ (ppm): 0.75-1.00 (12H, m), 1.10-1.50 (16H, m),1.69-1.85 (2H, m), 2.90-3.05 (4H, m), 7.24-7.38 (3H, m), 7.35-7.44 (3H,m), 7.90-7.95 (3H, m).

(Synthesis of Compound 12)

Next, using Compound 11, Compound 12 was synthesized as follows.

Under a nitrogen atmosphere, a mixture of Compound 10 (21.3 g),bis(pinacolate)diboron(4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane) (46.0 g),bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I) (0.24 g) (made bySigma-Aldrich Corporation), 4,4′-di-tert-butyl-2,2′-dipyridyl (0.19 g),and dioxane (140 mL) was stirred at 100° C. for 3 hours. After cooling,dioxane was distilled away under reduced pressure, and methanol (200 mL)was added to the residue; a precipitated solid was filtered out, anddried. The obtained solid was dissolved in toluene (250 mL), activatedclay (20 g) was added, and the solution was stirred at 60° C. for 30minutes. Then, the solution was filtered with a filter precoated withsilica gel while the solution was hot, and the obtained filtrate wascondensed under reduced pressure. Methanol (250 mL) was added to theobtained condensed product; a precipitated solid was filtered out, anddried to obtain 28.0 g of Compound 12 as a white powder.

LC-MS (ESI, positive): [M⁺]605.

¹H-NMR (300 MHz, CDCl₃) δ (ppm): 0.85-0.95 (12H, m), 1.24-1.50 (16H, m),1.66-1.85 (2H, m), 2.90-3.18 (4H, m), 7.60 (2H, s), 8.47 (2H, s).

(Synthesis of Compound 13)

Next, using Compound 12, Compound 13 was synthesized as follows.

Under a nitrogen atmosphere, copper bromide(II) (62.7 g) was added to amixed liquid of Compound 11 (28.0 g), dioxane (420 mL),N,N-dimethylformamide (420 mL), and water (210 mL), and stirring wasperformed at 95° C. for 2 hours. Further, copper bromide(II) (31.4 g)was added at the same temperature, and stirring was performed for 1.5hours. Then, copper bromide(II) (31.4 g) was further added at the sametemperature, and stirring was performed for 1.5 hours. The reactionsolution was cooled; hexane (300 mL) was added, and stirring wasperformed. Then, an organic layer was separated, and dried withmagnesium sulfate; the solvent was distilled away under reducedpressure. The residue was refined by silica gel column chromatography(developing solvent of hexane), and condensed to obtain a solid (21.0g). The obtained solid was dissolved in toluene (150 mL), activatedcarbon (5 g) was added, and stirring was performed at 60° C. for 30minutes. Then, the obtained mixture was filtered with a filter precoatedwith celite while the mixture was hot, and the obtained filtrate wascondensed under reduced pressure. The obtained condensed product wasrecrystallized with a mixed liquid of toluene and methanol to obtain13.2 g of Compound 12 as a white solid.

LC-MS (ESI, positive) [M⁺]511.

¹H-NMR (300 MHz, CDCl₃) δ (ppm): 0.80-0.98 (12H, m), 1.20-1.44 (16H, m),1.64-1.80 (2H, m), 2.77-2.95 (4H, m), 7.37 (2H, s), 8.00 (2H, s).

Example 3: Synthesis of Polymer Compound A1

Synthesis of a polymer (Polymer Compound A1) having the constitutionalunit represented by the following formula (K-1), the constitutional unitrepresented by the following formula (K-2), and the constitutional unitrepresented by the following formula (K-3) at a molar ratio of 5:50:45(a theoretical value based on prepared raw materials) was performed asfollows.

Under an argon atmosphere, Compound 5 synthesized in Example 1 (0.184 g,0.20 mmol), the compound (1.477 g, 2.00 mmol) represented by thefollowing formula (M-2-E):

the compound (0.987 g, 1.80 mmol) represented by the following formula(M-3-BR):

palladium acetate (1.35 mg), tris(o-methoxy phenyl)phosphine (14.8 mg),and toluene (44 mL) were mixed, and heated to 105° C. A 20% by weighttetraethylammonium hydroxide aqueous solution (6.9 g) was dropped intothe reaction solution, and refluxing was performed for 2 hours. Afterthe reaction, phenyl boronic acid (24.4 mg) and toluene (5 mL) wereadded thereto, and refluxing was further performed for 2 hours. Next, asodium diethyldithiocarbamate aqueous solution was added thereto, andstirring was performed at 80° C. for 2 hours. The obtained mixture wascooled, and toluene was prepared; the mixture was washed twice withwater, twice with a 3% by weight acetic acid aqueous solution, and twicewith water. The obtained solution was dropped into methanol, andfiltered to obtain a precipitate. This precipitate was dissolved intoluene, and the solution was passed through an alumina column and asilica gel column sequentially; thereby, the solution was refined. Theobtained solution was dropped into methanol, and stirred; the obtainedprecipitate was filtered out, and dried; thereby, 1.09 g of PolymerCompound A1 was obtained. The polystyrene-equivalent number-averagemolecular weight of Polymer Compound A1 was 9.80×10⁴, and thepolystyrene-equivalent weight-average molecular weight thereof was2.54×10⁵.

Example 4: Synthesis of Polymer Compound A2

Synthesis of a polymer (Polymer Compound A2) having the constitutionalunit represented by the following formula (K-1), the constitutional unitrepresented by the following formula (K-2), the constitutional unitrepresented by the following formula (K-3), and the constitutional unitrepresented by the following formula (K-4) at a molar ratio of5:50:25:20 (a theoretical value based on prepared raw materials) wasperformed as follows.

Under an argon atmosphere, Compound 5 synthesized in Example 1 (0.184 g,0.20 mmol), the compound (1.477 g, 2.00 mmol) represented by thefollowing formula (M-2-E):

the compound (0.548 g, 1.00 mmol) represented by the following formula(M-3-BR):

Compound 13 synthesized in Synthesis Example 1 (0.408 g, 0.80 mmol),palladium acetate (1.35 mg), tris(o-methoxy phenyl)phosphine (14.8 mg),and toluene (44 mL) were mixed, and heated to 105° C. A 20% by weighttetraethylammonium hydroxide aqueous solution (6.9 g) was dropped intothe reaction solution, and refluxing was performed for 2 hours. Afterthe reaction, phenyl boronic acid (24.4 mg) and toluene (5 mL) wereadded thereto, and refluxing was further performed for 2 hours. Next, asodium diethyldithiocarbamate aqueous solution was added thereto, andstirring was performed at 80° C. for 2 hours. The obtained mixture wascooled, and toluene was prepared; the mixture was washed twice withwater, twice with a 3% by weight acetic acid aqueous solution, and twicewith water. The obtained solution was dropped into methanol, andfiltered to obtain a precipitate. The precipitate was dissolved intoluene, and the solution was passed through an alumina column and asilica gel column sequentially; thereby, the solution was refined. Theobtained solution was dropped into methanol, and stirred; the obtainedprecipitate was filtered out, and dried; thereby, 1.90 g of PolymerCompound A2 was obtained. The polystyrene-equivalent number-averagemolecular weight of Polymer Compound A2 was 9.5×10⁴, and thepolystyrene-equivalent weight-average molecular weight thereof was2.60×10⁵.

Example 5: Synthesis of Polymer Compound A3

Synthesis of a polymer (Polymer Compound A3) having the constitutionalunit represented by the following formula (K-5), the constitutional unitrepresented by the following formula (K-2), the constitutional unitrepresented by the following formula (K-3), and the constitutional unitrepresented by the following formula (K-6) at a molar ratio of 3:50:45:2(a theoretical value based on prepared raw materials) was performed asfollows.

Under an argon atmosphere, Compound 10 synthesized in Example 2 (0.134g, 0.12 mmol), the compound (1.477 g, 2.00 mmol) represented by thefollowing formula (M-2-E):

the compound (0.987 g, 1.80 mmol) represented by the following formula(M-3-BR):

the compound (0.088 g, 0.08 mmol) represented by the following formula(M-6-BR):

palladium acetate (1.35 mg), tris(o-methoxy phenyl)phosphine (14.8 mg),and toluene (44 mL) were mixed, and heated to 105° C. A 20% by weighttetraethylammonium hydroxide aqueous solution (6.9 g) was dropped intothe reaction solution, and refluxing was performed for 2 hours. Afterthe reaction, phenyl boronic acid (24.4 mg) and toluene (5 mL) wereadded thereto, and refluxing was further performed for 2 hours. Next, asodium diethyldithiocarbamate aqueous solution was added thereto, andstirring was performed at 80° C. for 2 hours. The obtained mixture wascooled, and toluene was prepared; the mixture was washed twice withwater, twice with a 3% by weight acetic acid aqueous solution, and twicewith water. The obtained solution was dropped into methanol, andfiltered to obtain a precipitate. The precipitate was dissolved intoluene, and the solution was passed through an alumina column and asilica gel column sequentially; thereby, the solution was refined. Theobtained solution was dropped into methanol, and stirred; the obtainedprecipitate was filtered out, and dried; thereby, 1.40 g of PolymerCompound A3 was obtained. The polystyrene-equivalent number-averagemolecular weight of Polymer Compound A3 was 1.39×10⁵, and thepolystyrene-equivalent weight-average molecular weight thereof was4.13×10⁵.

Example 6: Synthesis of Polymer Compound A4

Synthesis of a polymer (Polymer Compound A4) having the constitutionalunit represented by the following formula (K-1), the constitutional unitrepresented by the following formula (K-2), the constitutional unitrepresented by the following formula (K-7), and the constitutional unitrepresented by the following formula (K-8) at a molar ratio of3:37:50:10 (a theoretical value based on prepared raw materials) wasperformed as follows.

Under an argon atmosphere, Compound 5 synthesized in Example 1 (0.111 g,0.12 mmol), the compound (0.954 g, 1.48 mmol) represented by thefollowing formula (M-2-BR):

the compound (0.997 g, 2.00 mmol) represented by the following formula(M-7-E):

the compound (0.254 g, 0.40 mmol) represented by the following formula(M-8-BR):

palladium acetate (1.35 mg), tris(o-methoxy phenyl)phosphine (14.8 mg),and toluene (44 mL) were mixed, and heated to 105° C. A 20% by weighttetraethylammonium hydroxide aqueous solution (6.9 g) was dropped intothe reaction solution, and refluxing was performed for 2 hours. Afterthe reaction, phenyl boronic acid (24.4 mg) and toluene (5 mL) wereadded thereto, and refluxing was further performed for 2 hours. Next, asodium diethyldithiocarbamate aqueous solution was added thereto, andstirring was performed at 80° C. for 2 hours. The obtained mixture wascooled, and toluene was prepared; the mixture was washed twice withwater, twice with a 3% by weight acetic acid aqueous solution, and twicewith water. The obtained solution was dropped into methanol, andfiltered to obtain a precipitate. The precipitate was dissolved intoluene, and the solution was passed through an alumina column and asilica gel column sequentially; thereby, the solution was refined. Theobtained solution was dropped into methanol, and stirred; the obtainedprecipitate was filtered out, and dried; thereby, 1.10 g of PolymerCompound A4 was obtained. The polystyrene-equivalent number-averagemolecular weight of Polymer Compound A4 was 8.2×10⁴, and thepolystyrene-equivalent weight-average molecular weight thereof was2.22×10⁵.

Synthesis Example 2: Synthesis of Polymer Compound AA

Synthesis of a polymer (Polymer Compound AA) having the constitutionalunit represented by the following formula (K-101), the constitutionalunit represented by the following formula (K-102), and theconstitutional unit represented by the following formula (K-3) at amolar ratio of 42:8:50 (a theoretical value based on prepared rawmaterials) was performed as follows.

Under an argon atmosphere, the compound (17.57 g, 33.13 mmol)represented by the following formula (M-3-Z):

the compound (12.88 g, 28.05 mmol) represented by the following formula(M-101-BR):

the compound (2.15 g, 5.01 mmol) represented by the following formula(M-102-BR):

palladium(II) acetate (7.4 mg), tris(2-methylphenyl)phosphine (70 mg), a0.74M toluene solution of quaternary ammonium chloride (Aliquat(registered trademark 336, made by Sigma-Aldrich Corporation, 3 g), andtoluene (200 g) were mixed.

A 18% by weight sodium carbonate aqueous solution (64 g) was droppedinto the mixed liquid; the mixed liquid was heated for 3 hours or moreand refluxed. After the reaction, phenylboronic acid (0.4 g) was addedto the mixed liquid, and refluxing was further performed for 5 hours ormore. Next, the reaction solution was diluted with toluene, and washedwith a 3% by weight acetic acid aqueous solution and ion exchange waterin this order; then, sodium diethyldithiocarbamate trihydrate (1.5 g)was added to the extracted organic layer, and stirred for 4 hours. Theobtained solution was refined by column chromatography using anequivalent mixture of alumina and silica gel as a stationary phase. Theobtained toluene solution was dropped into methanol, and stirred; theobtained precipitate was filtered out, and dried to obtain PolymerCompound AA. The polystyrene-equivalent number-average molecular weightof Polymer Compound AA was 8.9×10⁴, and the polystyrene-equivalentweight-average molecular weight thereof was 4.2×10⁵.

Example 7: Production and Evaluation of Light-Emitting Device 1

A film having a thickness of 35 nm was formed using a ethylene glycolmonobutyl ether/water=3/2 (volume ratio) mixed liquid ofpolythiophenesulfonic acid (Sigma-Aldrich Corporation, trade name:Plexcore OC 1200) by spin coating on a glass substrate on which an ITOfilm having a thickness of 45 nm was formed by a sputtering method, anddried on a hot plate at 170° C. for 15 minutes.

Next, Polymer Compound AA was dissolved in xylene to prepare a 0.7% byweight xylene solution. By spin coating using the xylene solution, afilm having a thickness of 20 nm was formed. This was heated on the hotplate in a nitrogen gas atmosphere at 180° C. for 60 minutes.

Next, Polymer Compound A1 was dissolved in xylene to prepare a 1.3% byweight xylene solution. By spin coating using the xylene solution, afilm having a thickness of 65 nm was formed; the film was dried byheating in the nitrogen atmosphere at 130° C. for 10 hours; then, as thecathode, approximately 3 nm of sodium fluoride, and then approximately80 nm of aluminum were vapor deposited to produce Light-EmittingDevice 1. The vapor deposition of the metal was started after the degreeof vacuum reached 1×10⁴ Pa or less.

Voltage was applied to the obtained Light-Emitting Device 1; EL lightemission having a peak at 445 nm was obtained from the device, and themaximum light emission efficiency was 6.3 cd/A. The results are shown inTable 1.

In the obtained Light-Emitting Device 1, the current value was set suchthat the initial luminance was 1000 cd/m²; then, Light-Emitting Device 1was driven at a constant current, and temporal change in luminance wasmeasured. As a result, the luminance reduced by half after 46 hours. Theresult is shown in Table 1.

Example 8: Production and Evaluation of Light-Emitting Device 2

Light-Emitting Device 2 was produced in the same manner as in Example 7except that Polymer Compound A2 was used instead of Polymer Compound A1in Example 7. Voltage was applied to the obtained Light-Emitting Device2; EL light emission having a peak at 450 nm was obtained from thedevice, and the maximum light emission efficiency was 7.4 cd/A. In theobtained Light-Emitting Device 2, the current value was set such thatthe initial luminance was 1000 cd/m²; then, Light-Emitting Device 2 wasdriven at a constant current, and temporal change in luminance wasmeasured. As a result, the luminance reduced by half after 134 hours.The result is shown in Table 1.

Example 9: Production and Evaluation of Light-Emitting Device 3

Light-Emitting Device 3 was produced in the same manner as in Example 7except that Polymer Compound A3 was used instead of Polymer Compound A1in Example 7. Voltage was applied to the obtained Light-Emitting Device3; EL light emission having a peak at 465 nm was obtained from thedevice, and the maximum light emission efficiency was 10.8 cd/A. In theobtained Light-Emitting Device 3, the current value was set such thatthe initial luminance was 1000 cd/m²; then, Light-Emitting Device 3 wasdriven at a constant current, and temporal change in luminance wasmeasured. As a result, the luminance reduced by half after 640 hours.The results are shown in Table 1.

Example 10: Production and Evaluation of Light-Emitting Device 4

Light-Emitting Device 4 was produced in the same manner as in Example 7except that instead of the xylene solution of Polymer Compound A1 inExample 7, a mixed solution in which a 1.3% by weight xylene solution ofPolymer Compound A1 and a 1.3% by weight xylene solution of the compoundrepresented by the following formula (T-1):

were mixed such that the weight ratio was 92.5:7.5 was used. Voltage wasapplied to the obtained Light-Emitting Device 4; EL light emissionhaving a peak at 625 nm was obtained from the device, and the maximumlight emission efficiency was 9.9 cd/A. In Light-Emitting Device 4obtained above, the current value was set such that the initialluminance was 1000 cd/m²; then, Light-Emitting Device 4 was driven at aconstant current, and temporal change in luminance was measured. As aresult, the luminance reduced by half after 7013 hours. The result isshown in Table 1.

Comparative Example 1: Synthesis of Polymer Compound B, and Productionand Evaluation of Light-Emitting Device C1

Synthesis of a polymer (Polymer Compound B) having the constitutionalunit represented by the following formula (K-9), the constitutional unitrepresented by the following formula (K-2), and the constitutional unitrepresented by the following formula (K-3) at a molar ratio of 5:50:45(a theoretical value based on prepared raw materials) was performed asfollows.

Under an argon atmosphere, the compound (0.326 g, 0.40 mmol) representedby the following formula (M-9-BR):

the compound (2.955 g, 4.00 mmol) represented by the following formula(M-2-E):

the compound (1.974 g, 3.60 mmol) represented by the following formula(M-3-BR):

palladium acetate (2.7 mg), tris(o-methoxy phenyl)phosphine (29.6 mg),quaternary ammonium chloride (Aliquat (registered trademark) 336, madeby Sigma-Aldrich Corporation, 0.52 g), and toluene (40 mL) were mixed,and heated to 105° C.

A 17.5% by weight sodium carbonate (10.9 mL) was dropped into thereaction solution, and refluxing was performed for 2.5 hours. After thereaction, phenyl boronic acid (50 mg) and toluene (5 mL) were addedthereto, and refluxing was further performed for 2 hours. Next, a sodiumdiethyldithiocarbamate aqueous solution was added thereto, and stirringwas performed at 80° C. for 2 hours. The obtained mixture was cooled,and toluene was prepared; the mixture was washed twice with water, twicewith a 3% by weight acetic acid aqueous solution, and twice with water.The obtained solution was dropped into methanol, and filtered to obtaina precipitate. The precipitate was dissolved in toluene, and thesolution was passed through an alumina column and a silica gel columnsequentially; thereby, the solution was refined. The obtained solutionwas dropped into methanol, and stirred; the obtained precipitate wasfiltered out, and dried; thereby, 2.04 g of Polymer Compound B wasobtained. The polystyrene-equivalent number-average molecular weight ofPolymer Compound B was 1.30×10⁵, and the polystyrene-equivalentweight-average molecular weight thereof was 3.20×10⁵.

Light-Emitting Device C1 was produced in the same manner as in Example 7except that Polymer Compound B was used instead of Polymer Compound A1in Example 7. Voltage was applied to the obtained Light-Emitting DeviceC1; EL light emission having a peak at 440 nm was obtained from thedevice, and the maximum light emission efficiency was 5.6 cd/A. In theobtained Light-Emitting Device C1, the current value was set such thatthe initial luminance was 1000 cd/m²; then, Light-Emitting Device C1 wasdriven at a constant current, and temporal change in luminance wasmeasured. As a result, the luminance reduced by half after 29 hours. Theresults are shown in Table 1.

Comparative Example 2: Synthesis of Polymer Compound C, And, Productionand Evaluation of Light-Emitting Device C2

Synthesis of a polymer (Polymer Compound C) having the constitutionalunit represented by the following formula (K-10), the constitutionalunit represented by the following formula (K-2), and the constitutionalunit represented by the following formula (K-3) at a molar ratio of5:50:45 (a theoretical value based on prepared raw materials) wasperformed as follows.

Under an argon atmosphere, the compound (0.168 g, 0.20 mmol) representedby the following formula (M-10-BR):

the compound (1.477 g, 2.00 mmol) represented by the following formula(M-2-E):

the compound (0.987 g, 1.80 mmol) represented by the following formula(M-3-BR):

palladium acetate (1.35 mg), tris(o-methoxy phenyl)phosphine (14.8 mg),and toluene (44 mL) were mixed, and heated to 105° C. A 20% by weighttetraethylammonium hydroxide aqueous solution (6.9 g) was dropped intothe reaction solution, and refluxing was performed for 3 hours. Afterthe reaction, phenyl boronic acid (24.4 mg) and toluene (5 mL) wereadded thereto, and refluxing was further performed for 18 hours. Next, asodium diethyldithiocarbamate aqueous solution was added thereto, andstirring was performed at 80° C. for 2 hours. The obtained mixture wascooled, and toluene was prepared; the mixture was washed twice withwater, twice with a 3% by weight acetic acid aqueous solution, and twicewith water. The obtained solution was dropped into methanol, andfiltered to obtain a precipitate. The precipitate was dissolved intoluene, and the solution was passed through an alumina column and asilica gel column sequentially; thereby, the solution was refined. Theobtained solution was dropped into methanol, and stirred; the obtainedprecipitate was filtered out, and dried; thereby, 1.28 g of PolymerCompound C was obtained. The polystyrene-equivalent number-averagemolecular weight of Polymer Compound C was 7.8×10⁴, and thepolystyrene-equivalent weight-average molecular weight thereof was2.16×10⁵.

Light-Emitting Device C2 was produced in the same manner as in Example 7except that Polymer Compound C was used instead of Polymer Compound A1in Example 7. Voltage was applied to the obtained Light-Emitting DeviceC2; EL light emission having a peak at 445 nm was obtained from thedevice, and the maximum light emission efficiency was 4.7 cd/A. In theobtained Light-Emitting Device C2, the current value was set such thatthe initial luminance was 1000 cd/m²; then, Light-Emitting Device C2 wasdriven at a constant current, and temporal change in luminance wasmeasured. As a result, the luminance reduced by half after less than 1hours. The results are shown in Table 1.

Comparative Example 3: Production and Evaluation of Light-EmittingDevice C3

Light-Emitting Device C3 was produced in the same manner as in Example 7except that instead of the xylene solution of Polymer Compound A1 inExample 7, a mixed solution in which a 1.3% by weight xylene solution ofPolymer Compound B and a 1.3% by weight xylene solution of the compoundrepresented by the above formula (T-1) were mixed such that the weightratio was 92.5:7.5 was used. Voltage was applied to the obtainedLight-Emitting Device C3; EL light emission having a peak at 625 nm wasobtained from the device, and the maximum light emission efficiency was8.8 cd/A. In Light-Emitting Device C3 obtained above, the current valuewas set such that the initial luminance was 1000 cd/m²; then,Light-Emitting Device C3 was driven at a constant current, and temporalchange in luminance was measured. As a result, the luminance reduced byhalf after 4039 hours. The result is shown in Table 1.

TABLE 1 The Triplet maximum Light Luminance Light- light- light emissionemission peak half-decay emitting Polymer emitting efficiency wavelengthlifetime device compound complex (cd/A) (nm) (hours) Example 7 1 A1 —6.3 445 46 Example 8 2 A2 — 7.4 450 134 Example 9 3 A3 — 10.8 465 640Example 10 4 A1 T1 9.9 625 7013 Comparative C1 B — 5.6 440 29 Example 1Comparative C2 C — 4.7 445 Less than 1 Example 2 hour Comparative C3 BT1 8.8 625 4039 Example 3

Examples 7, 8, and 9 correspond to Comparative Examples 1 and 2. InTable 1 above, Example 10 corresponds to Comparative Example 3.Apparently from Table 1 above, it turns out that the polymer compoundaccording to the present invention is useful for production of thelight-emitting device which is excellent in luminance life.

REFERENCE SIGNS LIST

10 . . . substrate, 11 . . . anode, 12 . . . hole injection layer, 13 .. . hole transport layer, 14 . . . light-emitting layer, 15 . . .electron transport layer, 16 . . . electron injection layer, 17 . . .cathode, 20 . . . substrate, 21 . . . anode, 22 . . . hole injectionlayer, 23 . . . light-emitting layer, 24 . . . cathode, 25 . . .protective layer, 100 . . . light-emitting device, 110 . . .light-emitting device, 200 . . . surface lighting source.

The invention claimed is:
 1. A polymer compound comprising aconstitutional unit represented by the following formula (1):

wherein n¹ and n² each independently represent an integer of 1 to 5; R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ each independently represent ahydrogen atom, an unsubstituted or substituted alkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group,or an unsubstituted or substituted monovalent heterocyclic group; R^(A)and R^(B) each independently represent a hydrogen atom, an unsubstitutedor substituted alkyl group, an unsubstituted or substituted aryl group,or an unsubstituted or substituted monovalent heterocyclic group; Ar¹and Ar² each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or differentoptionally substituted groups selected from the group consisting ofarylene groups and divalent heterocyclic groups are linked; when R¹, R²,R³, and R⁴ exist in plural, the plurality of R¹, R², R³, or R⁴ can bethe same or different from each other; among R¹, R², R³, and R⁴,adjacent groups can be linked to each other to form a ring structure;among R⁷, R⁸, R⁹ and R¹⁰, adjacent groups can be linked to each other toform a ring structure; Ar¹ and R^(A) can be linked to each other to forma ring structure; and Ar² and R^(B) can be linked to each other to forma ring structure, wherein the polymer compound further comprises aconstitutional unit represented by the following formula (2):

wherein Ar³ represents an unsubstituted or substituted arylene group, anunsubstituted or substituted divalent heterocyclic group, or a divalentgroup in which two or more same or different optionally substitutedgroups selected from the group consisting of arylene groups and divalentheterocyclic groups are linked, and wherein a content of theconstitutional unit represented by the formula (1) is 0.1 mol % to 5 mol% of the total constitutional units in the polymer compound.
 2. Thepolymer compound according to claim 1, wherein at least one of theconstitutional units represented by the formula (2) is a constitutionalunit consisting of an unsubstituted or substituted fluorenediyl group.3. The polymer compound according to claim 2, wherein at least one ofthe constitutional units represented by the formula (2) is aconstitutional unit consisting of an unsubstituted or substituted2,7-fluorenediyl group.
 4. The polymer compound according to claim 1,wherein at least one of the constitutional units represented by theformula (2) is a constitutional unit consisting of at least one groupselected from the group consisting of an unsubstituted or substitutedphenylene group, an unsubstituted or substituted naphthalenediyl group,an unsubstituted or substituted anthracenediyl group, and groupsrepresented by the following formula (3′):

wherein a¹ and a² each independently represent an integer of 0 to 4; a³represents an integer of 0 to 5; R¹¹, R¹², and R¹³ each independentlyrepresent an unsubstituted or substituted alkyl group, an unsubstitutedor substituted alkoxy group, an unsubstituted or substituted aryl group,an unsubstituted or substituted aryloxy group, an unsubstituted orsubstituted monovalent heterocyclic group, an unsubstituted orsubstituted alkoxycarbonyl group, an unsubstituted or substituted silylgroup, a halogen atom, a carboxyl group, or a cyano group; and when R¹¹,R¹², R¹³, and R¹⁴ exist in plural, the plurality of R¹¹, R¹², R¹³, orR¹⁴ can be the same or different from each other.
 5. The polymercompound according to claim 1, further comprising a constitutional unitrepresented by the following formula (4):

wherein b¹ and b² each independently represent 0 or 1; Ar⁴, Ar⁵, Ar⁶,and Ar⁷ each independently represent an unsubstituted or substitutedarylene group, an unsubstituted or substituted divalent heterocyclicgroup, or a divalent group in which two or more same or differentoptionally substituted groups selected from the group consisting ofarylene groups and divalent heterocyclic groups are linked; R^(C),R^(D), and R^(E) each independently represent a hydrogen atom, anunsubstituted or substituted alkyl group, an unsubstituted orsubstituted aryl group, or an unsubstituted or substituted monovalentheterocyclic group; Ar⁴, Ar⁵, Ar⁶, and Ar⁷ each can be linked to a groupother than the group to form a ring structure, the other group beingbonded to a nitrogen atom to which the group is bonded; and theconstitutional unit represented by the formula (4) is different from theconstitutional unit represented by the formula (1).
 6. The polymercompound according to claim 5, wherein at least one of theconstitutional units represented by the formula (4) is a constitutionalunit represented by the following formula (5):

wherein R^(F) represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, an unsubstituted or substituted aryl group, oran unsubstituted or substituted monovalent heterocyclic group; X¹represents a single bond, an oxygen atom, a sulfur atom, or a grouprepresented by —C(R¹⁴)₂—, wherein R¹⁴ represents an unsubstituted orsubstituted alkyl group or an unsubstituted or substituted aryl group,and a plurality of R¹⁴ can be the same or different from each other. 7.The polymer compound according to claim 5, comprising the constitutionalunit represented by the formula (1), the constitutional unit representedby formula (2), the constitutional unit represented by the formula (4),a constitutional unit consisting of an unsubstituted or substitutedfluorenediyl group, and a constitutional unit represented by anunsubstituted or substituted phenylene group.
 8. The polymer compoundaccording to claim 5, comprising the constitutional unit represented bythe formula (1), the constitutional unit represented by formula (2), theconstitutional unit represented by the formula (4), a constitutionalunit consisting of an unsubstituted or substituted fluorenediyl group,and a constitutional unit consisting of an unsubstituted or substitutednaphthalenediyl group.
 9. The polymer compound according to claim 5,comprising the constitutional unit represented by the formula (1), theconstitutional unit represented by formula (2), the constitutional unitrepresented by the formula (4), a constitutional unit consisting of anunsubstituted or substituted fluorenediyl group, and a constitutionalunit consisting of an unsubstituted or substituted anthracenediyl group.10. The polymer compound according to claim 5, comprising theconstitutional unit represented by the formula (1), the constitutionalunit represented by formula (2), the constitutional unit represented bythe formula (4), a constitutional unit consisting of an unsubstituted orsubstituted fluorenediyl group, and a constitutional unit represented bythe following formula (3):

wherein a¹ and a² each independently represent an integer of 0 to 4; a³represents an integer of 0 to 5; R¹¹, R¹², and R¹³ each independentlyrepresent an unsubstituted or substituted alkyl group, an unsubstitutedor substituted alkoxy group, an unsubstituted or substituted aryl group,an unsubstituted or substituted aryloxy group, an unsubstituted orsubstituted monovalent heterocyclic group, an unsubstituted orsubstituted alkoxycarbonyl group, an unsubstituted or substituted silylgroup, a halogen atom, a carboxyl group, or a cyano group; and when R¹¹,R¹², R¹³, and R¹⁴ exist in plural, the plurality of R¹¹, R¹², R¹³, orR¹⁴ can be the same or different from each other.
 11. The polymercompound according to claim 1, wherein n¹ and n² in the formula (1) eachindependently represent 3 or
 4. 12. The polymer compound according toclaim 11, wherein R^(A) and R^(B) in the formula (1) each independentlyrepresent an unsubstituted or substituted aryl group or an unsubstitutedor substituted monovalent heterocyclic group.
 13. The polymer compoundaccording to claim 1, wherein the polymer compound is synthesized bycondensation polymerization of a monomer (1) that introduces theconstitutional unit represented by the formula (1) with a monomer (X)that introduces a constitutional unit different from the constitutionalunit represented by the formula (1), and when the number of the monomer(1) is N₁ and the number of the monomer (X) is N_(X), N₁ and N_(X)satisfy the following equation (I):0.1≦N ₁×100/(N ₁ +N _(X))≦5  (I).
 14. A composition comprising thepolymer compound according to claim 1, and at least one selected fromthe group consisting of a hole transport material, an electron transportmaterial, and a light-emitting material.
 15. The composition accordingto claim 14, comprising a triplet light-emitting complex as thelight-emitting material.
 16. A liquid composition comprising the polymercompound according to claim 1, and a solvent.
 17. An organic filmcomprising the polymer compound according to claim
 1. 18. An organicfilm prepared using the composition according to claim
 14. 19. Alight-emitting device having the organic film according to claim
 17. 20.A surface lighting source having the light-emitting device according toclaim
 19. 21. A display device having the light-emitting deviceaccording to claim
 19. 22. The polymer compound according to claim 12,wherein R¹, R², R³, and R⁴ each independently represent a hydrogen atom,or an unsubstituted or substituted alkyl group.
 23. The polymer compoundaccording to claim 22, wherein R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ eachindependently represent a hydrogen atom, an unsubstituted or substitutedalkyl group, or an unsubstituted or substituted aryl group.
 24. Thepolymer compound according to claim 23, wherein Ar¹ and Ar² eachindependently represent an unsubstituted or substituted arylene group,or an unsubstituted or substituted divalent heterocyclic group.